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A Highly Reactive and Stereoselective β‐Mannopyranosylation System: Mannosyl 4‐Pentenoate/PhSeOTf
Author(s) -
Baek Ju Yuel,
Choi Tae Jin,
Jeon Heung Bae,
Kim Kwan Soo
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200602642
Subject(s) - stereoselectivity , acceptor , chemistry , stereochemistry , linkage (software) , combinatorial chemistry , organic chemistry , biochemistry , catalysis , gene , physics , condensed matter physics
Controlled linkage : PhSeOTf‐promoted glycosylations of a variety of acceptor alcohols with 4,6‐ O ‐benzylidene‐2,3‐di‐ O ‐benzylmannopyranosyl pentenoate afford β‐mannopyranosides in high yields and with excellent stereoselectivity (see scheme). This method is even better than other known methods for the mannosylation of simple reactive primary alcohols. Tf=trifluoromethanesulfonyl, TTBP=2,4,6‐tri‐ tert ‐butylpyrimidine.