Premium
Dual Stereoselectivity of 1‐(2′‐Carboxy)benzyl 2‐Deoxyglycosides as Glycosyl Donors in the Direct Construction of 2‐Deoxyglycosyl Linkages
Author(s) -
Kim Kwan Soo,
Park Jin,
Lee Yong Joo,
Seo Yong Sung
Publication year - 2003
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.200390139
Subject(s) - stereoselectivity , glycosyl , glycosylation , chemistry , glycosyl donor , stereochemistry , organic chemistry , catalysis , biochemistry
Different protecting groups on the glycosyl donor changes the stereoselectivity of the new glycosylation reaction shown in the scheme. Glycosylation of CB 4,6‐ O ‐benzylidene‐2‐deoxyglycoside 1 with secondary alcohol acceptors gave predominantly β‐disaccharides 3 , whereas the same reaction with CB tri‐ O ‐benzyl‐2‐deoxyglycoside 2 afforded α‐disaccharides 4 . CB=(2′‐carboxy)benzyl.