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Facile and Effective Synthesis of Glucopyranosyl Oligosacchardes with Alternative (1 →3)‐α‐ and ‐β‐Linkages in the Presence of C‐2 Ester Capable of Neighboring Group Participation
Author(s) -
Zeng Ytag,
Mng Jun,
Kong FanZuo
Publication year - 2002
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20020201103
Subject(s) - chemistry , tetrasaccharide , acetylation , glycosylation , acceptor , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , polysaccharide , physics , gene , condensed matter physics
Coupling of acetylated α‐(1 → 3)‐linked glucobiosyl trichloroacetimidate with acetylated α‐(1→3)‐linked glucobioside acceptor gave a β‐linked tetrasaccharide, while coupling of acetylated β‐(1→3)‐linked glucobiosyl trichloroacetimidate with acetylated β‐(1→3)‐linked glucobioside acceptor gave an α‐linked tetrasaccharide in spite of the C‐2 neighboring group participation. Two hexasaccharides with alternative (1→3)‐α‐and ‐β‐linkges were synthesized by these reactions via remote control exerted by the glycosylation bond in either donor or acceptor.