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

Bando, Masafumi; Kawasaki, Yuri; Nagata, Osamu; Okada, Yasunori; Ikuta, Daiki; Ikeuchi, Kazutada; Yamada, Hidetoshi

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

Bando, Masafumi; Kawasaki, Yuri; Nagata, Osamu et al.

Chemical & pharmaceutical bulletin, 2021, 69(1), 124-140

Permalink : https://hdl.handle.net/2115/80418

このアイテムのアクセス数:586件（2026-08-12 05:58 集計）

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https://doi.org/10.1248/cpb.c20-00733			11

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アクセス権	open access
URI	https://hdl.handle.net/2115/80418
タイトル	beta-Selective Glycosylation Using Axial-Rich and 2-O-Rhamnosylated Glucosyl Donors Controlled by the Protecting Pattern of the Second Sugar
著者	Bando, Masafumi ; Kawasaki, Yuri ; Nagata, Osamu ; Okada, Yasunori ; Ikuta, Daiki ; Ikeuchi, Kazutada ; Yamada, Hidetoshi
著者名 Bando, Masafumi
著者名 Kawasaki, Yuri
著者名 Nagata, Osamu
著者名 Okada, Yasunori
著者名 Ikuta, Daiki
e-Rad_Researcher 70756676 著者名 Ikeuchi, Kazutada
著者名 Yamada, Hidetoshi
言語	英語
キーワード	2-O-ramnosylated glucose donor
	beta-selective glycosylation
	axial-rich
	bulky silyl group
	protecting group effect
発行日	2021-01
出版者	The Pharmaceutical Society of Japan （日本薬学会）
収録物名	Chemical & pharmaceutical bulletin
巻(号)	69(1)
ページ	124-140
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Version of Record
PISSN	0009-2363
関連情報 (isIdenticalTo)	出版社版DOI https://doi.org/10.1248/cpb.c20-00733