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β‐Selective Glycosylation by Using O ‐Aryl‐Protected Glycosyl Donors
Author(s) -
Otsuka Yuji,
Yamamoto Toshihiro,
Fukase Koichi
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900700
Subject(s) - glycosylation , glycosyl , glycosyl donor , aryl , chemistry , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , alkyl
New glycosyl donors have been developed that contained several para ‐substituted O ‐aryl protecting groups and their stereoselectivity for the glycosylation reaction was evaluated. A highly β‐selective glycosylation reaction was achieved by using thioglycosides that were protected by 4‐nitrophenyl (NP) groups, which were introduced by using the corresponding diaryliodonium triflate. Analysis of the stereoselectivities of several glycosyl donors indicated that the β‐glycosides were obtained through an S N 2‐type displacement from the corresponding α‐glycosyl triflate. The NP group could be removed by reduction of the nitro group and acylation, followed by oxidation with ceric ammonium nitrate (CAN).