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Hokkaido University Collection of Scholarly and Academic Papers >
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Peer-reviewed Journal Articles, etc >
beta-Selective Glycosylation Using Axial-Rich and 2-O-Rhamnosylated Glucosyl Donors Controlled by the Protecting Pattern of the Second Sugar
| Title: | beta-Selective Glycosylation Using Axial-Rich and 2-O-Rhamnosylated Glucosyl Donors Controlled by the Protecting Pattern of the Second Sugar |
| Authors: | Bando, Masafumi Browse this author | | Kawasaki, Yuri Browse this author | | Nagata, Osamu Browse this author | | Okada, Yasunori Browse this author | | Ikuta, Daiki Browse this author | | Ikeuchi, Kazutada Browse this author →KAKEN DB | | Yamada, Hidetoshi Browse this author |
| Keywords: | 2-O-ramnosylated glucose donor | | beta-selective glycosylation | | axial-rich | | bulky silyl group | | protecting group effect |
| Issue Date: | Jan-2021 |
| Publisher: | The Pharmaceutical Society of Japan （日本薬学会） |
| Journal Title: | Chemical & pharmaceutical bulletin |
| Volume: | 69 |
| Issue: | 1 |
| Start Page: | 124 |
| End Page: | 140 |
| Publisher DOI: | 10.1248/cpb.c20-00733 |
| Abstract: | Herein, we describe two counterexamples of the previously reported beta/alpha-selectivity of 96/4 for glycosylation using ethyl 2-O-[2,3,4-tris-O-ter(-butyldimethylsilyl (TBS)-alpha-L-rhamnopyranosyl]-3,4,6-tris-O-TBS-thio-beta-D-glucopyranoside as the glycosyl donor. Furthermore, we investigated the effects of protecting group on the rhamnose moieties in the glycosylation with cholestanol and revealed that beta-selectivity originated from the two TBS groups at the 3-O and 4-O positions of rhamnose. In contrast, the TBS group at the 2-O position of rhamnose hampered the beta-selectivity. Finally, the beta/alpha-selectivity during the glycosylation was enhanced to >= 99/1. The results obtained herein suggest that the protecting groups on the sugar connected to the 2-O of a glycosyl donor with axial-rich conformation can control the stereoselectivity of glycosylation. |
| Type: | article |
| URI: | http://hdl.handle.net/2115/80418 |
| Appears in Collections: | 理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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