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Stereoselective Synthesis of α‐3‐Deoxy‐ D ‐ manno ‐oct‐2‐ulosonic Acid (α‐Kdo) Glycosides Using 5,7‐ O ‐Di‐ tert ‐butylsilylene‐Protected Kdo Ethyl Thioglycoside Donors
Author(s) -
Huang JiaSheng,
Huang Wei,
Meng Xue,
Wang Xin,
Gao PengCheng,
Yang JinSong
Publication year - 2015
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.201505176
Subject(s) - glycosidic bond , glycoside , glycosyl , chemistry , stereoselectivity , stereochemistry , glycosyl donor , selectivity , organic chemistry , catalysis , enzyme
An efficient methodology for the synthesis of α‐Kdo glycosidic bonds has been developed with 5,7‐ O ‐di‐ tert ‐butylsilylene (DTBS) protected Kdo ethyl thioglycosides as glycosyl donors. The approach permits a wide scope of acceptors to be used, thus affording biologically significant Kdo glycosides in good to excellent chemical yields with complete α‐selectivity. The synthetic utility of an orthogonally protected Kdo donor has been demonstrated by concise preparation of two α‐Kdo‐containing oligosaccharides.