Unexpected Role of O-2 “Protecting” Groups of Glycosyl Donors in Mediating Regioselective Glycosidation
- 8 March 2002
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (13), 3198-3199
- https://doi.org/10.1021/ja012383m
Abstract
Glycosidation of several vicinal diols reveals that exquisite regioselectivity can be achieved by using 2-O-benzoyl n-pentenyl glycoside donors and/or their cyclic 1,2-ortho ester counterparts. The regioselective preferences for both are the same, although ratios and yields may differ. In stark contrast, glycosidation of the diols with the corresponding 2-O-benzylated donors gives poor, if any, regioselectivity.Keywords
This publication has 8 references indexed in Scilit:
- Targeted Glycosyl Donor Delivery for Site-Selective Glycosylation,1Organic Letters, 2000
- Synthesis of Carbohydrate-Antigenic Structures ofMycobacterium Tuberculosisusing an Iodonium Ion Promoted Glycosidation ApproachJournal of Carbohydrate Chemistry, 1990
- CorrigendumAngewandte Chemie-International Edition, 1985
- Regioselektive Glycosidierung von Lactose durch unterschiedliche Katalysatorsysteme. Synthese der Saccharid-Sequenzen von asialo-GM 1 - und asialo-GM 2-GangliosidenCarbohydrate Research, 1984
- Chemistry of the glycosidic linkage. An efficient synthesis of 1,2-trans-di-saccharidesCarbohydrate Research, 1977
- Preparation and Synthetic Utility of Some Organotin Derivatives of nucleosidesThe Journal of Organic Chemistry, 1974
- Simplified Preparation of Sophorose (2-O-β-D-glucopyranosyl-D-glucose)The Journal of Organic Chemistry, 1961
- Chemistry of the Carbohydrates and GlycosidesAnnual Review of Biochemistry, 1940