É. Bozó, J. Kuszmann
Apr 7, 2000
Citations
0
Influential Citations
7
Citations
Journal
Carbohydrate Research
Abstract
Abstract Tri- O -acetyl-5-thio- d -ribopyranosyl bromide was converted into 3,4-di- O -benzoyl-1,5-anhydro-5-thio- d - erythro -pent-1-enitol (3,4-di- O -benzoyl-5-thio- d -ribal), the azidonitration of which afforded an unstable mixture of 2-azido-3,4-di- O -benzoyl-2-deoxy-1- O -nitro-5-thio- d -pentopyranoside isomers. This was converted without separation into the corresponding 1- O -acetyl derivatives from which an α,β anomeric mixture of the 1- O -acetyl-2-azido-3,4-di- O -benzoyl-2-deoxy-5-thio- d -arabinopyranose isomers could be isolated in high yield. Glycosidation of this mixture with 4-cyano- or 4-nitrobenzenethiol, using trimethylsilyl triflate or boron trifluoride etherate, respectively, as promoters gave the corresponding β anomers exclusively. Zemplen debenzoylation afforded 4-cyanophenyl as well as 4-nitrophenyl 2-azido-2-deoxy-1,5-dithio-β- d -arabinopyranoside, respectively. When 1- O -acetyl-2-azido-3,4-di- O -benzoyl-2-deoxy-5-thio- d -lyxopyranose was used as glycosyl donor only the corresponding β anomers, i.e., 4-cyanophenyl as well as 4-nitrophenyl 2-azido-2-deoxy-1,5-dithio-β- d -lyxopyranosides, could be isolated after Zemplen debenzoylation in high yield. All four 1,5-dithioglycosides possess significant oral antithrombotic activity.