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Search for "nucleoside chemistry" in Full Text gives 10 result(s) in Beilstein Journal of Organic Chemistry.
Synthetic strategies toward 1,3-oxathiolane nucleoside analogues
- Umesh P. Aher,
- Dhananjai Srivastava,
- Girij P. Singh and
- Jayashree B. S
Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182
Graphical Abstract
Figure 1: Representative modified 1,3-oxathiolane nucleoside analogues.
Figure 2: Mechanism of antiviral action of 1,3-oxathiolane nucleosides, 3TC (1) and FTC (2), as chain termina...
Figure 3: Synthetic strategies for the construction of the 1,3-oxathiolane sugar ring.
Scheme 1: Synthesis of 4 from benzoyloxyacetaldehyde (3a) and 2-mercapto-substituted dimethyl acetal 3na.
Scheme 2: Synthesis of 8 from protected glycolic aldehyde 3b and 2-mercaptoacetic acid (3o).
Scheme 3: Synthesis of 20 from ᴅ-mannose (3c).
Scheme 4: Synthesis of 20 from 1,6-thioanhydro-ᴅ-galactose (3d).
Scheme 5: Synthesis of 8 from 2-(tert-butyldiphenylsilyloxy)methyl-5-oxo-1,2-oxathiolane (3m).
Scheme 6: Synthesis of 20a from ʟ-gulose derivative 3f.
Scheme 7: Synthesis of 31 from (+)-thiolactic acid 3p and 2-benzoyloxyacetaldehyde (3a).
Scheme 8: Synthesis of 35a from 1,4-dithiane-2,5-diol (3q) and glyoxylic acid (3g) hydrate.
Scheme 9: Synthetic routes toward 41 through Pummerer reaction from methyl 2-mercaptoacetate (3j) and bromoac...
Scheme 10: Strategy for the synthesis of 2,5-substituted 1,3-oxathiolane 41a using 4-nitrobenzyl glyoxylate an...
Scheme 11: Synthesis of 44 by a resolution method using Mucor miehei lipase.
Scheme 12: Synthesis of 45 from benzoyloxyacetaldehyde (3a) and 2-mercaptoacetaldehyde bis(2-methoxyethyl) ace...
Scheme 13: Synthesis of 46 from 2-mercaptoacetaldehyde bis(2-methoxyethyl) acetal (3nc) and diethyl 3-phosphon...
Scheme 14: Synthesis of 48 from 1,3-dihydroxyacetone dimer 3l.
Scheme 15: Approach toward 52 from protected alkene 3rb and lactic acid derivative 51 developed by Snead et al....
Scheme 16: Recent approach toward 56a developed by Kashinath et al.
Scheme 17: Synthesis of 56a from ʟ-menthyl glyoxylate (3h) hydrate by DKR.
Scheme 18: Possible mechanism with catalytic TEA for rapid interconversion of isomers.
Scheme 19: Synthesis of 35a by a classical resolution method through norephedrine salt 58 formation.
Scheme 20: Synthesis of 63 via [1,2]-Brook rearrangement from silyl glyoxylate 61 and thiol 3nb.
Scheme 21: Combined use of STS and CAL-B as catalysts to synthesize an enantiopure oxathiolane precursor 65.
Scheme 22: Synthesis of 1 and 1a from glycolaldehyde dimer 64 and 1,4-dithiane-2,5-diol (3q) using STS and CAL...
Scheme 23: Synthesis of 68 by using Klebsiella oxytoca.
Scheme 24: Synthesis of 71 and 72 using Trichosporon taibachii lipase and kinetic resolution.
Scheme 25: Synthesis of 1,3-oxathiolan-5-ones 77 and 78 via dynamic covalent kinetic resolution.
Figure 4: Pathway for glycosidic bond formation.
Scheme 26: First synthesis of (±)-BCH-189 (1c) by Belleau et al.
Scheme 27: Enantioselective synthesis of 3TC (1).
Scheme 28: Synthesis of cis-diastereomer 3TC (1) from oxathiolane propionate 44.
Scheme 29: Synthesis of (±)-BCH-189 (1c) via SnCl4-mediated N-glycosylation of 8.
Scheme 30: Synthesis of (+)-BCH-189 (1a) via TMSOTf-mediated N-glycosylation of 20.
Scheme 31: Synthesis of 3TC (1) from oxathiolane precursor 20a.
Scheme 32: Synthesis of 83 via N-glycosylation of 20 with pyrimidine bases.
Scheme 33: Synthesis of 85 via N-glycosylation of 20 with purine bases.
Scheme 34: Synthesis of 86 and 87 via N-glycosylation using TMSOTf and pyrimidines.
Scheme 35: Synthesis of 90 and 91 via N-glycosylation using TMSOTf and purines.
Scheme 36: Synthesis of 3TC (1) via TMSI-mediated N-glycosylation.
Scheme 37: Stereoselective N-glycosylation for the synthesis of 1 by anchimeric assistance of a chiral auxilia...
Scheme 38: Whitehead and co-workers’ approach for the synthesis of 1 via direct N-glycosylation without an act...
Scheme 39: ZrCl4-mediated stereoselective N-glycosylation.
Scheme 40: Plausible reaction mechanism for stereoselective N-glycosylation using ZrCl4.
Scheme 41: Synthesis of enantiomerically pure oxathiolane nucleosides 1 and 2.
Scheme 42: Synthesis of tetrazole analogues of 1,3-oxathiolane nucleosides 97.
Scheme 43: Synthetic approach toward 99 from 1,3-oxathiolane 45 by Camplo et al.
Scheme 44: Synthesis of 100 from oxathiolane phosphonate analogue 46.
Scheme 45: Synthetic approach toward 102 and the corresponding cyclic thianucleoside monophosphate 102a by Cha...
Scheme 46: Synthesis of emtricitabine (2) from 1,4-dithiane-2,5-diol (3q) and glyoxylic acid (3g).
Scheme 47: Synthesis of 1 and 2, respectively, from 56a–d using iodine-mediated N-glycosylation.
Scheme 48: Plausible mechanism for silane- and I2-mediated N-glycosylation.
Scheme 49: Pyridinium triflate-mediated N-glycosylation of 35a.
Scheme 50: Possible pathway for stereoselective N-glycosylation via in situ chelation with a metal ligand.
Scheme 51: Synthesis of novel 1,3-oxathiolane nucleoside 108 from oxathiolane precursor 8 and 3-benzyloxy-2-me...
Scheme 52: Synthesis of 110 using T-705 as a nucleobase and 1,3-oxathiolane derivative 8 via N-glycosylation.
Scheme 53: Synthesis of 1 using an asymmetric leaving group and N-glycosylation with bromine and mesitylene.
Scheme 54: Cytidine deaminase for enzymatic separation of 1c.
Scheme 55: Enzymatic resolution of the monophosphate derivative 116 for the synthesis of (−)-BCH-189 (1) and (...
Scheme 56: Enantioselective resolution by PLE-mediated hydrolysis to obtain FTC (2).
Scheme 57: (+)-Menthyl chloroformate as a resolving agent to separate a racemic mixture 120.
Scheme 58: Separation of racemic mixture 1c by cocrystal 123 formation with (S)-(−)-BINOL.
Double-headed nucleosides: Synthesis and applications
- Vineet Verma,
- Jyotirmoy Maity,
- Vipin K. Maikhuri,
- Ritika Sharma,
- Himal K. Ganguly and
- Ashok K. Prasad
Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98
Graphical Abstract
Figure 1: Double-headed nucleosides. B1 and B2 = nucleobases or heterocyclic/carbocyclic moieties; L = linker....
Scheme 1: Synthesis of 2′-(pyrimidin-1-yl)methyl- or 2′-(purin-9-yl)methyl-substituted double-headed nucleosi...
Scheme 2: Synthesis of double-headed nucleoside 7 having two cytosine moieties.
Scheme 3: Synthesis of double-headed nucleoside 2′-deoxy-2′-C-(2-(thymine-1-yl)ethyl)-uridine (11).
Scheme 4: Double-headed nucleosides 14 and 15 obtained by click reaction.
Scheme 5: Synthesis of the double-headed nucleoside 19.
Scheme 6: Synthesis of the double-headed nucleosides 24 and 25.
Scheme 7: Synthesis of double-headed nucleosides 28 and 29.
Scheme 8: Synthesis of double-headed nucleoside 33.
Scheme 9: Synthesis of double-headed nucleoside 37.
Scheme 10: Synthesis of the double-headed nucleoside 1-(5′-O-(4,4′-dimethoxytrityl)-2′-C-((4-(pyren-1-yl)-1,2,...
Scheme 11: Synthesis of triazole-containing double-headed ribonucleosides 46a–c and 50a–e.
Scheme 12: Synthesis of double-headed nucleosides 54a–g.
Scheme 13: Synthesis of double-headed nucleosides 59 and 60.
Scheme 14: Synthesis of the double-headed nucleosides 63 and 64.
Scheme 15: Synthesis of double-headed nucleosides 66a–c.
Scheme 16: Synthesis of benzoxazole-containing double-headed nucleosides 69 and 71 from 5′-amino-5′-deoxynucle...
Scheme 17: Synthesis of 4′-C-((N6-benzoyladenin-9-yl)methyl)thymidine (75) and 4′-C-((thymin-1-yl)methyl)thymi...
Scheme 18: Synthesis of double-headed nucleosides 5′-(adenine-9-yl)-5′-deoxythymidine (79) and 5′-(adenine-9-y...
Scheme 19: Synthesis of double-headed nucleosides 85–87 via reversed nucleosides methodology.
Scheme 20: Double-headed nucleosides 91 and 92 derived from ω-terminal-acetylenic sugar derivatives 90a,b.
Scheme 21: Synthesis of double-headed nucleosides 96a–g.
Scheme 22: Synthesis of double-headed nucleosides 100 and 103.
Scheme 23: Double-headed nucleosides 104 and 105 with a triazole motif.
Scheme 24: Synthesis of the double-headed nucleosides 107 and 108.
Scheme 25: Synthesis of double-headed nucleoside 110 with additional nucleobase in 5′-(S)-C-position joined th...
Scheme 26: Synthesis of double-headed nucleosides 111–113 with additional nucleobases in the 5′-(S)-C-position...
Scheme 27: Synthesis of double-headed nucleoside 114 by click reaction.
Scheme 28: Synthesis of double-headed nucleosides 118 with an additional nucleobase at the 5′-(S)-C-position.
Scheme 29: Synthesis of bicyclic double-headed nucleoside 122.
Scheme 30: Synthesis of double-headed nucleosides 125a–c derived from 2′-amino-LNA.
Scheme 31: Double-headed nucleoside 127 obtained by click reaction.
Scheme 32: Synthesis of double-headed nucleoside 130.
Scheme 33: Double-headed nucleosides 132a–d and 134a–d synthesized by Sonogashira cross coupling reaction.
Scheme 34: Synthesis of double-headed nucleosides 137 and 138 via Suzuki coupling.
Scheme 35: Synthesis of double-headed nucleosides 140 and 141 via Sonogashira cross coupling reaction.
Scheme 36: Synthesis of double-headed nucleoside 143.
Scheme 37: Synthesis of the double-headed nucleoside 146.
Scheme 38: Synthesis of 5-C-alkynyl-functionalized double-headed nucleosides 151a–d.
Scheme 39: Synthesis of 5-C-triazolyl-functionalized double-headed nucleosides 154a, b.
Scheme 40: Synthesis of double-headed nucleosides 157a–c.
Scheme 41: Synthesis of double-headed nucleoside 159, phosphoramidite 160 and the corresponding nucleotide mon...
Scheme 42: Synthesis of double-headed nucleoside 163, phosphoramidite 164 and the corresponding nucleotide mon...
Scheme 43: Synthesis of double-headed nucleoside 167, phosphoramidite 168, and the corresponding nucleotide mo...
Scheme 44: Synthesis of double-headed nucleoside 171, phosphoramidite 172, and the corresponding nucleotide mo...
Scheme 45: Synthesis of double-headed nucleoside 175, phosphoramidite 176, and the corresponding nucleotide mo...
Scheme 46: Synthesis of double-headed nucleoside 178.
Scheme 47: Synthesis of the double-headed nucleosides 181 and 183.
Scheme 48: Alternative synthesis of the double-headed nucleoside 183.
Scheme 49: Synthesis of double-headed nucleoside 188 through thermal [2 + 3] sydnone–alkyne cycloaddition reac...
Scheme 50: Synthesis of the double-headed nucleosides 190 and 191.
Scheme 51: Synthesis of 1-((5S)-2,3,4-tri-O-acetyl-5-(2,6-dichloropurin-9-yl)-β-ᴅ-xylopyranosyl)uracil (195).
Scheme 52: Synthesis of hexopyranosyl double-headed pyrimidine homonucleosides 200a–c.
Figure 2: 3′-C-Ethynyl-β-ᴅ-allopyranonucleoside derivatives 201a–f.
Scheme 53: Synthesis of 3′-C-(1,4-disubstituted-1,2,3-triazolyl)-double-headed pyranonucleosides 203–207.
Scheme 54: Synthesis of 3′-C-(1,4-disubstituted-1,2,3-triazolyl)-double-headed pyranonucleosides 208 and 209.
Scheme 55: Synthesis of 3′-C-(1,4-disubstituted-1,2,3-triazolyl)-double-headed pyranonucleoside 210.
Scheme 56: Synthesis of double-headed acyclic nucleosides (2S,3R)-1,4-bis(thymine-1-yl)butane-2,3-diol (213a) ...
Scheme 57: Synthesis of double-headed acyclic nucleosides (2R,3S)-1,4-bis(thymine-1-yl)butane-2,3-diol (213c) ...
Scheme 58: Synthesis of double-headed acetylated 1,3,4-oxadiazino[6,5-b]indolium-substituted C-nucleosides 218b...
Scheme 59: Synthesis of double-headed acyclic nucleoside 222.
Scheme 60: Synthesis of functionalized 1,2-bis(1,2,4-triazol-3-yl)ethane-1,2-diols 223a–f.
Scheme 61: Synthesis of acyclic double-headed 1,2,4-triazino[5,6-b]indole C-nucleosides 226–231.
Scheme 62: Synthesis of double-headed 1,3,4-thiadiazoline, 1,3,4-oxadiazoline, and 1,2,4-triazoline acyclo C-n...
Scheme 63: Synthesis of double-headed acyclo C-nucleosides 240–242.
Scheme 64: Synthesis of double-headed acyclo C-nucleoside 246.
Scheme 65: Synthesis of acyclo double-headed nucleoside 250.
Scheme 66: Synthesis of acyclo double-headed nucleoside 253.
Scheme 67: Synthesis of acyclo double-headed nucleosides 259a–d.
Scheme 68: Synthesis of acyclo double-headed nucleoside 261.
Changed reactivity of secondary hydroxy groups in C8-modified adenosine – lessons learned from silylation
- Jennifer Frommer and
- Sabine Müller
Beilstein J. Org. Chem. 2020, 16, 2854–2861, doi:10.3762/bjoc.16.234
- being preferentially formed. Optimization of the protection scheme lead to a new and economic route to the desired C8-alkynylated building block and its incorporation in RNA. Keywords: nucleoside chemistry; protecting groups; RNA synthesis; Sonogashira reaction; Introduction Oligoribonucleotides
Graphical Abstract
Scheme 1: Synthesis of a C8-linker-modified adenosine derivative. (a) 4 equiv TBDMS-Cl, 5 equiv imidazole, DM...
Figure 1: Characterization and assignment of the TBDMS isomers via HSQC (red) and HMBC (blue) NMR measurement...
Scheme 2: New synthetic route to the C8-linker modified adenosine building block. (a) i) 1.2 equiv di-tert-bu...
Tuning the stability of alkoxyisopropyl protection groups
- Zehong Liang,
- Henna Koivikko,
- Mikko Oivanen and
- Petri Heinonen
Beilstein J. Org. Chem. 2019, 15, 746–751, doi:10.3762/bjoc.15.70
- . Some structural modifications have been introduced to overcome the chirality problem, e.g., the methoxytetrahydropyranyl group suggested in 1970’s for a substitute of THP in nucleoside chemistry [4][5]. For protection of highly sensitive compounds acetone-based acetals can be applied. However, of these
Graphical Abstract
Figure 1: Reagents for acetal protections.
Scheme 1: Synthesis of 2-alkoxyprop-2-yl-protected thymidines. Reagents and conditions (i) 7 equiv 1a–e, 0.5 ...
Figure 2: Enol ether 8a: R1 = TBS and 8b: R1 = H.
Scheme 2: Proposed acetal hydrolysis pathways.
Enzymatic separation of epimeric 4-C-hydroxymethylated furanosugars: Synthesis of bicyclic nucleosides
- Neha Rana,
- Manish Kumar,
- Vinod Khatri,
- Jyotirmoy Maity and
- Ashok K. Prasad
Beilstein J. Org. Chem. 2017, 13, 2078–2086, doi:10.3762/bjoc.13.205
- of synthetic carbohydrate and nucleoside chemistry. Experimental The Candida antarctica lipase-B (CAL-B or Novozyme®-435) immobilized on polyacrylate was purchased from Sigma-Aldrich Co. (USA). Theremomyces lanuginosus lipase (Lipozyme TL IM) immobilized on silica was obtained as a gift from
Graphical Abstract
Scheme 1: Formation of a 1:1 epimeric mixture of 3a and 3b.
Scheme 2: Lipase-catalysed separation of a mixture of ribo- and xylotrihydroxyfuranosides.
Figure 1: Screening of Novozyme®-435 and Lipozyme TL IM in different organic solvents at 35 °C for regioselec...
Figure 2: ORTEP diagram of tosylated sugar derivatives 5 and 10.
Scheme 3: Convergent synthesis of 3′-O,4′-C-methyleneuridine.
Scheme 4: Convergent synthesis of 2′-O,4′-C-methylene-xylouridine.
Figure 3: ORTEP diagram and preferential N-type sugar ring puckering of 2′-O,4′-C-methylene-xylouridine (14).
Multicomponent reactions in nucleoside chemistry
- Mariola Koszytkowska-Stawińska and
- Włodzimierz Buchowicz
Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179
- . An example of the application of the Kabachnik–Fields reaction in nucleoside chemistry represents the preparation of α-arylaminophosphonates 28 and 29 by Zhang et al. (Scheme 12) [76]. The reactions between 5-formyl-2'-deoxyuridine 27 (or its 3',5'-di-O-acetyl derivative 14), an aniline and dimethyl
- carbon atom. Conclusion In this comprehensive review application of multicomponent reactions (MCRs) in nucleoside chemistry has been presented. In recent years, growing interest in the construction of novel nucleoside scaffolds by MCR has been observed. This conclusion is supported by the fact that 23
Graphical Abstract
Figure 1: Selected chemical modifications of natural ribose or 2'-deoxyribose nucleosides leading to the deve...
Scheme 1: (a) Classical Mannich reaction; (b) general structures of selected hydrogen active components and s...
Scheme 2: Reagents and reaction conditions: i. H2O or H2O/EtOH, 60–100 °C, 7 h–10 d; ii. H2, Pd/C or PtO2; ii...
Scheme 3: Reagents and reaction conditions: i. H2O, 90 °C, overnight.
Scheme 4: Reagents and reaction conditions: i. AcOH, H2O, 60 °C, 12 h-5 d; ii. AcOH, H2O, 60 °C, 8 h.
Scheme 5: Reagents and reaction conditions: i. CuBr, THF, reflux, 0.5 h; ii. n-Bu4NF·3H2O, THF, rt, 2 h.
Scheme 6: Reagents and reaction conditions: i. [bmim][PF6], 80 °C, 5–8 h.
Scheme 7: Reagents and reaction conditions: i. EtOH, reflux, 24 h.
Scheme 8: Reagents and reaction conditions: i. NaOAc, H2O, 95 °C, 1–16 h; ii. NaOAc, H2O, 95 °C, 1 h.
Scheme 9: Reagents and reaction conditions: i. a. 37% aq HCl, MeOH; b. NaOAc, 1,4-dioxane, H2O, 100 °C, overn...
Scheme 10: Reagents and reaction conditions: i. DMAP, DCC, MeOH, rt, 1 h.
Scheme 11: The Kabachnik–Fields reaction.
Scheme 12: Reagents and reaction conditions: i. 60 °C, 3 h; ii. 80 °C, 2 h.
Scheme 13: The four-component Ugi reaction.
Scheme 14: Reagents and reaction conditions: i. MeOH, rt, 2–3 d, yields not given.
Scheme 15: Reagents and reaction conditions: i. MeOH/CH2Cl2 (1:1), rt, 24 h, yield not given; ii. 6 N aq HCl, ...
Scheme 16: Reagents and reaction conditions: i. MeOH/H2O, rt, 26 h; ii. aq AcOH, reflux, 50%; iii. reversed ph...
Scheme 17: Reagents and reaction conditions: i. MeOH, rt, 24 h; ii. HCl, MeOH, 0 °C to rt, 6 h, then H2O, rt, ...
Scheme 18: Reagents and reaction conditions: i. DMF/Py/MeOH (1:1:1), rt, 48 h; ii. 10% HCl/MeOH, rt, 30 min.
Scheme 19: Reagents and reaction conditions (R = CH3 or H): i. CH2Cl2/MeOH (2:1), 35–40 °C, 2 d; ii. HF/pyridi...
Scheme 20: Reagents and reaction conditions: i. MeOH, 76%; ii. 80% aq TFA, 100%.
Scheme 21: Reagents and reaction conditions: i. EtOH, rt, 72 h; ii. Zn, aq NaH2PO4, THF, rt, 1 week; then 80% ...
Scheme 22: Reagents and reaction conditions: i. EtOH, rt, 48 h, then silica gel chromatography, 33% for 57 (30...
Scheme 23: Reagents and reaction conditions: i. [bmim]BF4, 80 °C, 4 h; ii. [bmim]BF4, 80 °C, 3 h; iii. [bmim]BF...
Scheme 24: Reagents and reaction conditions: i. [bmim]BF4, 80 °C.
Scheme 25: Reagents and reaction conditions: i. H3PW12O40 (2 mol %), EtOH, 50 °C, 2–15 h; ii. H3PW12O40 (2 mol...
Scheme 26: General scheme of the Biginelli reaction.
Scheme 27: Reagents and reaction conditions: i. EtOH, reflux.
Scheme 28: Reagents and reaction conditions: i. Bu4N+HSO4−, diethylene glycol, 120 °C, 1.5–3 h.
Scheme 29: Reagents and reaction conditions: i. BF3·Et2O, CuCl, AcOH, THF, 65 °C, 24 h; ii. Yb(OTf)3, THF, ref...
Scheme 30: Reagents and reaction conditions: TCT (10 mol %), rt: i. 100 min; ii. 150 min; iii. 140 min.
Scheme 31: Reagents and reaction conditions: i. EtOH, microwave irradiation (300 W), 10 min; ii. EtOH, 75 °C, ...
Scheme 32: The Hantzsch reaction.
Scheme 33: Reagents and reaction conditions: TCT (10 mol %), rt, 80–150 min.
Scheme 34: Reagents and reaction conditions: i. Yb(OTf)3, THF, 90 °C, 12 h; ii. 4 Å molecular sieves, EtOH, 90...
Scheme 35: Reagents and reaction conditions: i. MeOH, 50 °C, 48 h.
Scheme 36: Reagents and reaction conditions: i. MeOH, 25 °C, 5 d.
Scheme 37: Bu4N+HSO4−, diethylene glycol, 80 °C, 1–2 h.
Scheme 38: The three-component carbopalladation of dienes on the example of buta-1,3-diene.
Scheme 39: Reagents and reaction conditions: i. 5 mol % Pd(dba)2, Bu4NCl, ZnCl2, acetonitrile or DMSO, 80 °C o...
Scheme 40: Reagents and reaction conditions: i. 2.5 mol % Pd2(dba)3, tris(2-furyl)phosphine, K2CO3, MeCN or DM...
Scheme 41: Reagents and reaction conditions: i. 2.5 mol % Pd2(dba)3, tris(2-furyl)phosphine, K2CO3, MeCN or DM...
Scheme 42: The three-component Bucherer–Bergs reaction.
Scheme 43: Reagents and reaction conditions: i. MeOH, H2O, 70 °C, 4.5 h; ii. (1) H2, 5% Pd/C, MeOH, 55 °C, 5 h...
Scheme 44: Reagents and reaction conditions: i. pyridine, MgSO4, 100 °C, 28 h, N2; ii. DMF, 70–90 °C, 22–30 h,...
Scheme 45: Reagents and reaction conditions: i. Montmorillonite K-10 clay, microwave irradiation (600 W), 6–10...
Scheme 46: Reagents and reaction conditions: i. Montmorillonite K-10 clay, microwave irradiation (560 W), 6–10...
Scheme 47: Reagents and reaction conditions: i. CeCl3·7H2O (20 mol %), NaI (20 mol %), microwave irradiation (...
Scheme 48: Reagents and reaction conditions: i. PhI(OAc)2 (3 mol %), microwave irradiation (45 °C), 6–9 min.
Scheme 49: Reagents and reaction conditions: i. 117, ethyl pyruvate, TiCl4, dichloromethane, −78 °C, 1 h; then ...
Concise total synthesis of two marine natural nucleosides: trachycladines A and B
- Haixin Ding,
- Wei Li,
- Zhizhong Ruan,
- Ruchun Yang,
- Zhijie Mao,
- Qiang Xiao and
- Jun Wu
Beilstein J. Org. Chem. 2014, 10, 1681–1685, doi:10.3762/bjoc.10.176
- yield. The reaction is a novel instance of the broad substrate tolerance of AMPDA and extends its usage in nucleoside chemistry. Therefore, trachycladine B was synthesized in 35.0% overall yield from 5-deoxy-1,2,3-tri-O-acetyl-β-D-ribofuranose (6). Next, the coupling of carbohydrate 4 with 2,6
Graphical Abstract
Figure 1: Structures of trachycladine A and B.
Figure 2: Retrosynthetic analysis of trachycladines A and B.
Scheme 1: Synthesis of 5-deoxy-1-O-acetyl-2,3-di-O-benzoyl-2-C-β-methyl-D-ribofuranose (4). Reagents and cond...
Figure 3: The X-ray crystal structural of 1-O-methyl-3-O-(2,4-dichlorobenzyl)-5-deoxy-α-D-ribofuranose (9).
Scheme 2: Synthesis of trachycladine B (2). Reagents and conditions: (a) i. N,O-Bis(trimethylsilyl)acetamide ...
Scheme 3: Synthesis of trachycladine A (1). Reagents and conditions: (a) DBU, TMSOTf, CH3CN, 86%; (b) NH3 sat...
Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)
- Sabin Llona-Minguez and
- Simon P. Mackay
Beilstein J. Org. Chem. 2014, 10, 1333–1338, doi:10.3762/bjoc.10.135
- medicinal chemistry literature reveals >200 publications in the field. Additionally, PreQ0 meets all the criteria dictated by the “2-0” rule of kinase-likeness proposed by Aronov et al. [8]. It is likely that compounds derived from PreQ0 display kinase activity. 7-Deazapurine nucleoside chemistry has been
Graphical Abstract
Figure 1: Biosynthetic pathway leading to nucleosides queuosine and archaeosine.
Figure 2: Chemical structure of noraristeromycin.
Figure 3: Synthesis of PreQ0 and chloro-intermediate 9. Reagents and conditions: (a) Methyl formate, NaOMe, P...
Figure 4: Synthesis of 15, a (1RS,2SR,3RS)-3-aminocyclopentane-1,2-diol derivative of PreQ0. Reagents and con...
Figure 5: Synthesis of 16, a (1S,2R,3S,4R)-4-aminocyclopentane-1,2,3-triol derivative of PreQ0. Reagents and ...
Figure 6: Synthesis of 21 and 22, 3-arylcyclohexylamine derivatives of PreQ0. Reagents and conditions: (a) Ph...
Oxalyl retro-peptide gelators. Synthesis, gelation properties and stereochemical effects
- Janja Makarević,
- Milan Jokić,
- Leo Frkanec,
- Vesna Čaplar,
- Nataša Šijaković Vujičić and
- Mladen Žinić
Beilstein J. Org. Chem. 2010, 6, 945–959, doi:10.3762/bjoc.6.106
- Janja Makarevic Milan Jokic Leo Frkanec Vesna Caplar Natasa Sijakovic Vujicic Mladen Zinic Laboratory for Supramolecular and Nucleoside Chemistry, Ruđer Bošković Institute, P.O.B. 180, HR-10002 Zagreb, Croatia 10.3762/bjoc.6.106 Abstract In this work we report on gelation properties, self
Graphical Abstract
Scheme 1: Oxalyl retro-dipetide gelators; each b to a, (a) LiOH/MeOH, H2O; (b) H+; each b to c: (c) NH3/MeOH.
Figure 1: Chiral bis(amino acid)-(I) and bis(amino alcohol)-(II)-oxalamide gelators.
Figure 2: TEM images (PWK staining) of: (S,S)-1a H2O/DMSO gel.
Figure 3: TEM images (PWK staining) of: (S,R)-1a H2O/DMSO gel.
Figure 4: TEM images (PWK staining) of: (S,R)-1b toluene gel showing the presence of short tape like aggregat...
Figure 5: The concentration dependence of NH and C*H chemical shifts in (S,R)-1b toluene-d8 gel samples (conc...
Figure 6: The concentration dependence of NH and C*H chemical shifts in (S,S)-1b and its racemate (S,S)-1b/(R...
Figure 7: Temperature dependence of: a) oxalamide NH protons (▲), Leu-NH protons (Δ) and b) oxalamide-α-Leu-C...
Figure 8: Temperature dependent CD spectra of: a) (S,R)-1b decalin gel (c = 3.4·10−2 M); b) (S,S)-1b decalin ...
Figure 9: X-ray powder diffractograms of (a) (S,R)-1b and (b) (S,S)-1b xerogels prepared from their toluene g...
Figure 10: (a) Fully minimized the lowest energy conformations of (S,S)-1b (top) and (S,R)-1b generated by sys...
Figure 11: Schematic presentation of the proposed (S,S)-1b and (S,R)-1b basic packing model based on XRPD, 1H ...
Figure 12: X-ray powder diffraction (XRPD) diagram of (S,R)-1a water/DMSO xerogel.
Synthesis of some novel hydrazono acyclic nucleoside analogues
- Mohammad N. Soltani Rad,
- Ali Khalafi-Nezhad and
- Somayeh Behrouz
Beilstein J. Org. Chem. 2010, 6, No. 49, doi:10.3762/bjoc.6.49
- antineoplastic (e.g. bisantrene [4][10]), contain a hydrazone moiety in their structure. Furthermore, various structurally related miconazole bioactive hydrazones are known as antimicrobial and antifungal agents [11][12]. The significance of nucleoside chemistry in drug discovery is well-known and fully
Graphical Abstract
Figure 1: Chemical structures of miconazole (A), oxiconazole (B) and hydrazono acyclic nucleoside analogue (C...
Scheme 1: Synthetic pathway for hydrazono acyclic nucleoside 2a–2g.
Scheme 2: Synthetic pathway for hydrazono acyclic nucleoside 2h–2o.
