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Search for "4-DMAP" in Full Text gives 9 result(s) in Beilstein Journal of Organic Chemistry.
Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones
Beilstein J. Org. Chem. 2020, 16, 2304–2313, doi:10.3762/bjoc.16.191
- replacement of pyridine by other organic bases/ligands (4-DMAP, 2,2’-bipy, Et3N, TMEDA, 8-hydroxyquinoline) resulted in poorer yields of the target product in all cases (Table 1, entries 6–10). The use of copper(II) fluoride (in contrast to triflate) instead of acetate had practically no effect on the
Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica
Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189
- hydroxy group more acidic and thus a better leaving group in the reaction. Next, the quaternary 11α-hydroxy group was acylated by freshly prepared 5-azidopentanoic anhydride in the presence of 4-DMAP at room temperature. Finally, the azidopentanoate 4 was successively introduced into a click reaction with
- °C) after which the DCU was filtered out. 11α-Deacetylarchangelolide (60 mg, 0.12 mmol) and 4-DMAP (18 mg, 0.14 mmol) were dissolved in CH2Cl2 (3 mL) and freshly prepared anhydride of 5-azidopentanoic acid was added to the stirred solution. The mixture was stirred at room temperature for 8 h, after
- , Abingdon, UK) following manufacturer protocol. Statistical analysis Analysis of variance (ANOVA) and graphical presentation of data were done using GraphPad Prism 6.05, San Diego, CA. Abbreviations 4-DMAP, 4-(N,N-dimethylamino)pyridine; AcOEt, ethyl acetate; DCC, dicyclohexylcarbodiimide; DCU
Novel unit B cryptophycin analogues as payloads for targeted therapy
Beilstein J. Org. Chem. 2018, 14, 1281–1286, doi:10.3762/bjoc.14.109
- , rt, overnight; (c) NaI, acetone, reflux, overnight; (d) TsCl, Et3N, CH2Cl2, rt, overnight; (e) NaI, acetone, reflux, overnight; (f) 6 or 9, K2CO3, DMF, 50 °C, overnight; (g) LiOH, H2O/MeOH/THF 1:1:1, rt, 2 h. Synthesis of cryptophycin analogues 22, 23 and 24. Reagents and conditions: (a) 4-DMAP
A semisynthesis of 3'-O-ethyl-5,6-dihydrospinosyn J based on the spinosyn A aglycone
Beilstein J. Org. Chem. 2017, 13, 2603–2609, doi:10.3762/bjoc.13.257
- selectively protected by TBDMSCl in the presence of 4-DMAP in dry dichloromethane, presumably due to the steric hindrance around C17. Then C17–O-protected compound 6 was prepared by using TIPSOTf as protecting reagent in the presence of 2,6-lutidine in dry dichloromethane. Due to the different stabilities of
BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide
Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128
- ]amine) [37] in DMF gave a cholesterol-containing clickate 4 in 49% yield. The pegylation of 4 with amino-PEG4-alkyne in the presence of EDCI (N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride), 4-DMAP (4-dimethylaminopyridine) and HOBt (N-hydroxybenzotriazole) in DMF provided an alkyne
Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope
Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15
- (bottom); fluorescence intensity (y-axis) vs counts of cells (x-axis). Reagents and conditions: (A) p-thiocresol, BF3∙Et2O, CH2Cl2, 24 h, rt, 81%; (B) i) NaOMe, MeOH, 12 h, rt; ii) benzaldehyde dimethylacetal, p-TsOH, DMF/MeCN 1:1, 18 h; 60 °C; iii) Ac2O, 4-DMAP, pyridine, 12 h, rt, 85% (3 steps); (C) i
- ) aq 80% AcOH, 3 h, 90 °C; ii) TrtCl, 4-DMAP, pyridine, 24 h, 50 °C, 83% (2 steps); (D) i) Tf2O, pyridine, CH2Cl2, 2 h, 0 °C; ii) TBAF, MS 4 Å, THF, 3 h, rt, 70% (2 steps); iii) aq 80% AcOH, 4 h, 90 °C; iv) Ac2O, pyridine, 4-DMAP, 12 h, rt, 78% (2 steps); (E) AgOTf, NIS, MS 4 Å, 24 h, 0 °C, 80%; (F) i
Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition
Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308
- that CuAAC catalysis with [(SIMes)CuCl] can be notably improved by addition of aromatic nitrogen donor ligands [149]. For example, fast homogeneous catalysis in water/alcohol solvent mixtures is possible with [(SIMes)CuCl] in the presence of 4-DMAP or 1,10-phenanthroline (Scheme 11). The catalyst
Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine
Beilstein J. Org. Chem. 2010, 6, No. 73, doi:10.3762/bjoc.6.73
- SK10 2NA, United Kingdom 10.3762/bjoc.6.73 Abstract The effects on the redox properties of modifying the molecular skeleton of neutral bis-2-(4-dimethylamino)pyridinylidene electron donors, derived from 4-dimethylaminopyridine (4-DMAP), have been explored, by varying two parameters: (i) the length of
- at the 4 and 4′ positions led to only slight changes in the redox potentials. Keywords: dication; 4-DMAP; electron donor; electron transfer; radical cation; redox; reduction; Introduction Neutral organic compounds 1 and 4–10 (Figure 1) have attracted considerable attention as ground-state electron
- DMF) [22][23][24][25] and the 4-dimethylaminopyridine (4-DMAP)-derived donor 8 [E1/2 (DMF) = −1.69 V vs Fc/Fc+] [26][27][28][29], which would equate to −1.24 V vs SCE [E (DMF)Fc/Fc+ = 0.45 V vs SCE] [41] react with aryl iodides to afford aryl anions. As an indication of their enhanced donor properties
2-Phenyl- tetrahydropyrimidine- 4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids
Beilstein J. Org. Chem. 2009, 5, No. 43, doi:10.3762/bjoc.5.43
- consists of a 4-DMAP catalysed N-acylation reaction with acyl chlorides and usually affords the target compounds in moderate yields [39][40]. We chose Nα-Cbz-protected β-alanine amide (3) as starting material for the synthesis of the 2-phenyltetrahydropyrimidine-4(1H)-one rac-4 to circumvent the difficulty
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