STEREOSELECTIVE SYNTHESIS OF 1,2-CIS-GLYCOFURANOSIDES USING GLYCOFURANOSYL FLUORIDES
- 5 June 1983
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 12 (6) , 935-938
- https://doi.org/10.1246/cl.1983.935
Abstract
1,2-cis-Ribofuranosides are stereoselectively synthesized in high yields by the reaction of β-ribofuranosyl fluoride and alcohols in the presence of stannous chloride and trityl perchlorate. Under similar condition, α-arabinofuranosyl fluoride reacts with cholestanol to give 1,2-cis-arabinofuranoside predominatly.Keywords
This publication has 12 references indexed in Scilit:
- Improved synthesis of .alpha.-D-ribofuranosides via stereoselective alkylation of a dibutylstannylene derivative for ready access to the 2-substituted 2-deoxyarabinofuranosidesThe Journal of Organic Chemistry, 1982
- Advances in Selective Chemical Syntheses of Complex OligosaccharidesAngewandte Chemie International Edition in English, 1982
- New Synthetic Reactions Based on the Onium Salts of Aza‐Arenes [New synthetic methods (29)]Angewandte Chemie International Edition in English, 1979
- α‐Verknüpfte Di‐ und Trisaccharide der D‐RibofuranoseEuropean Journal of Inorganic Chemistry, 1979
- Facile, Highly Selective Synthesis of α‐ and β‐Disaccharides from 1‐O‐Metalated D‐RibofuranosesAngewandte Chemie International Edition in English, 1979
- A novel synthesis of 1,2-cis-disaccharidesJournal of the American Chemical Society, 1977
- Halide ion catalyzed glycosidation reactions. Syntheses of .alpha.-linked disaccharidesJournal of the American Chemical Society, 1975
- Syntheses of α-D-linked disaccharidesCarbohydrate Research, 1975
- 2,3,5-Tri-O-benzyl-D-ribosyl and -L-arabinosyl BromidesThe Journal of Organic Chemistry, 1961
- Notes- Improved Preparation of Triphenylmethyl Perchlorate and Fluoroborate for Use in Hydride Ion Exchange ReactionsThe Journal of Organic Chemistry, 1960