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beta-Selective Glycosylation Using Axial-Rich and 2-O-Rhamnosylated Glucosyl Donors Controlled by the Protecting Pattern of the Second Sugar

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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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