An Efficient Method for the Stereoselective Synthesis of β-d- and α-d-Ribofuranosides from 2,3,5-Tri-O-benzyl-d-ribofuranose by the Use of [Catecholato(2−)-O,O′]oxotitanium and Trifluoromethanesulfonic Anhydride
- 1 April 1993
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 66 (4) , 1211-1215
- https://doi.org/10.1246/bcsj.66.1211
Abstract
β-D-Ribofuranosides are stereoselectively synthesized in high yields directly from 2,3,5-tri-O-benzyl-D-ribofuranose and trimethylsilylated nucleophiles by the use of [catecholato(2−)-O,O′ ]oxotitanium and trifluoromethanesulfonic anhydride, while α-D-ribofuranosides are prepared predominantly in high yields in the coexistence of lithium perchlorate.Keywords
This publication has 5 references indexed in Scilit:
- The Use of Grignard Reagents in the Synthesis of Carbohydrates. III. The One-way Anomerization of Methyl Glycofuranosides and the Opening of Their Furanose RingsBulletin of the Chemical Society of Japan, 1981
- 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
- Chemistry of the glycosidic linkage.O-glycosylations catalyzed by stannic chloride, in the D-ribofuranose and D-glucopyranose seriesCarbohydrate Research, 1977
- 2,3,5-Tri-O-benzyl-D-ribosyl and -L-arabinosyl BromidesThe Journal of Organic Chemistry, 1961