Abstract
1,2-cis-Glycosides are frequently found in many biologically active natural products and pharmaceutical compounds. Therefore, to elucidate the precise biological roles of these carbohydrates and structure-activity relationships, the development of efficient glycosylation methods for the stereoselective synthesis of 1,2-cis-glycosides is becoming increasingly important in synthetic organic chemistry. In this review article, development of boronic-acid-catalyzed regioselective and 1,2-cis-stereoselective glycosylation that was recently developed in our laboratory, is introduced. This glycosylation method was successfully applied to the regioselective and stereoselective formation of 1,2-cis-β-glycosidic linkages, to the efficient synthesis of complex glycosides, and to the direct regioselective and 1,2-cis-stereoselective glycosylation of unprotected glycosides. Furthermore, mechanistic studies were consistent with a highly dissociative concerted SNi mechanism.
Original language | English |
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Pages (from-to) | 221-231 |
Number of pages | 11 |
Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
Volume | 78 |
Issue number | 3 |
DOIs | |
Publication status | Published - 2020 Jan 1 |
Keywords
- 1,2-Cis-glycoside
- Borinic acid
- Boronic acid
- Direct modification
- Glycosylation
- Natural glycoside
- Organoboron catalyst
- Regioselective
- Stereoselective
- Unprotected glycoside
ASJC Scopus subject areas
- Organic Chemistry