Search results
Search for "azidolysis" in Full Text gives 6 result(s) in Beilstein Journal of Organic Chemistry.
Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr4/PPh3 and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior
Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9
- from the stereochemistry of the standard Appel mechanism due to participation of the Δ5 π-electrons. In contrast, the subsequent azidolysis (NaN3/DMF) of 3β-bromocholest-5-ene proceeds predominantly by Walden inversion (SN2) affording 3α-azidocholest-5-ene. The structures of all relevant products were
- –517. Keywords: Appel reaction; azidolysis; cholesterol; crystal structure; Walden inversion; Introduction 3β-Hydroxycholest-5-ene (cholesterol) is a structural and physiologic amphipathic steroid in human and animals as well. Cholesterol is an essential component of the plasma membrane, where it
Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol
Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163
- group in compound 10 was converted to the corresponding alcohol 11 as the sole isomer via SN2 substitution by hydrolysis. In the azidolysis reaction of compound 8, we propose that because the azide group is bulkier than the water molecule, it could not substitute the second mesylate group, and therefore
Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives
Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7
- -oxabicyclo[5.2.1]decan-10-yl)carbamate was confirmed by X-ray diffraction. Keywords: aminocyclitol; azidolysis; bicyclic β-lactam; bicyclic lactone; cyclic β-amino acids; DFT; Introduction Cyclic β-amino acids have for the past few decades aroused widespread synthetic interest owing to their diverse
Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides
Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85
- C2, can be accomplished by nucleophilic fluorination and azidolysis starting from dianhydro derivatives 1 and 2 as we described previously [26]. The resulting intermediates 3 can be transformed into 2-azidohexopyranosides 4 by cleavage of the internal acetal and protection of the anomeric position
Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine
Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75
- :2,3-dianhydro-4-O-benzyl-β-D-mannopyranose (10, one of the Černý epoxides available from D-glucal [31][32][33] or levoglucosan [34]). Regioselective azidolysis [21][35][36] of 10 yielded 2-azido alcohol 11 which was converted to 12 by benzoylation at O-3 and debenzylation at O-4. To prevent azide
- ] of 14 followed by azidolysis [41] furnished 15. 2-Azido-3,4-epoxide 18 was prepared from readily available [42] 2,3-isopropylidene-D-mannosan (16) in five steps (Scheme 2). Tosylation of 16 [43], followed by hydrolysis of the benzylidene acetal [44] and oxirane ring closure [45] at C-4 delivered 1,6
- :3,4-dianhydro derivative 17. Formation of the triflate ester and azidolysis furnished 1,6:3,4-dianhydro-2-azido derivative 18. Lithium azide was found superior to sodium azide in conversion of the triflate to the azide 18, and the yield of 18 increased from 48% reported earlier [46] to 82%. The
Synthesis and surface grafting of a β-cyclodextrin dimer facilitating cooperative inclusion of 2,6-ANS
Beilstein J. Org. Chem. 2015, 11, 514–523, doi:10.3762/bjoc.11.58
- (d, 2H), 2.94 (d, 2H), 2.79 (t, 1H). Surface grafting: Optically transparent silica slides were preactivated with azidosilane monolayers for the CuAAC grafting by vapor deposition of GPTMS (−800 mbar, 48 h, 105 °C) in 400 mM sodium azide in PEG400 [27] for 4 h at 40 °C. Following azidolysis, the
Other Beilstein-Institut Open Science Activities
