Synthesis of glycofuranosides from S-glycofuranosyl dithiocarbonates (xanthates) and dithiocarbamates

Coupling reactions between an anomeric mixture of S-ribofuranosyl N, N-diethyldithiocarbamate ( 1b) as the donor and 1,2:3,4-di- O-isopropylidene- α- d-galactopyranose or 1,6-anhydro-3,4- O-isopropylidene- β- d-galactopyranose as the acceptor in the presence of silver triflate afforded β-d-ribofuran...

Full description

Saved in:
Bibliographic Details
Published in:Carbohydrate research 1996-12, Vol.295, p.235-243
Main Authors: Bogusiak, Jadwiga, Szeja, Wieslaw
Format: Article
Language:English
Subjects:
Dithiocarbamates
Dithiocarbonates
Glycofuranosides
Glycofuranosyl donors
Glycosylation
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Coupling reactions between an anomeric mixture of S-ribofuranosyl N, N-diethyldithiocarbamate ( 1b) as the donor and 1,2:3,4-di- O-isopropylidene- α- d-galactopyranose or 1,6-anhydro-3,4- O-isopropylidene- β- d-galactopyranose as the acceptor in the presence of silver triflate afforded β-d-ribofuranosyl disaccharides in good yield. Application of this glycosidation methodology for the synthesis of alkylglycofuranoside derivatives of d-xylofuranose and l-arabinofuranose resulted in the 1,2- trans configurated products with moderate to high stereoselectivity.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(96)90148-2