Simple and mild stereoselective O-glycosidation using 1,2-anhydrosugars under neutral conditions |
| |
| Authors: | Devaraj Somasundaram Kalpattu K. Balasubramanain Bhagavathy Shanmugasundaram |
| |
| Affiliation: | 1. Department of Chemistry, B.S. Abdur Rahman Crescent Institute of Science and Technology, Vandalur, Chennai 600015, India;2. Department of Biotechnology, Indian Institute of Technology Madras, Guindy, Chennai 600048, India |
| |
| Abstract: | The ring opening of α-d-1,2-anhydrohexapyranoses with phenols proceeded smoothly in ethyl acetate (neutral conditions) in the absence of metal ion catalysts or additives to stereoselectively furnish 1,2-cis-α-aryl glycosides as the major product and 1,2-trans-β-aryl glycosides as the minor product in good yields. Under similar conditions, this ring opening reaction with alcohols afforded exclusively β-alkyl glycosides in excellent yields. |
| |
| Keywords: | 1,2-Anhydrosugars Glycal epoxide Aromatic glycosylation Aryl glycosides Alkyl glycosides |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
