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

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...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-09, Vol.54 (37), p.10894-10898
Main Authors: Huang, Jia-Sheng, Huang, Wei, Meng, Xue, Wang, Xin, Gao, Peng-Cheng, Yang, Jin-Song
Format: Article
Language:English
Subjects:
acetals
Butanes - chemistry
carbohydrates
Glycosides - chemical synthesis
Glycosides - chemistry
glycosylation
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
silanes
Silanes - chemistry
Stereoisomerism
synthesis design
Thioglycosides - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. A Kdo K.O.: The title compound is a common structural constituent of polysaccharides present in bacteria. An approach to stereospecific synthesis of α‐Kdo glycosides was developed by using 5,7‐O‐di‐tert‐butylsilylene‐protected Kdo ethyl thioglycoside donors (1). Various α‐Kdo glycosidic linkages were constructed in good to excellent chemical yields with complete α‐selectivity (2). M.S.=molecular sieves, NIS=N‐iodosuccinimide, Tf=trifluoromethanesulfonyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201505176