Anomeric Reactivity-Based One-Pot Oligosaccharide Synthesis:  A Rapid Route to Oligosaccharide Libraries

The assembly of an oligosaccharide library has been achieved in a practical and efficient manner employing a one-pot sequential approach. With the help of the anomeric reactivity values of thioglycosides, using a thioglycoside (mono- or disaccharide) with one free hydroxyl group as acceptor and dono...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-04, Vol.65 (8), p.2410-2431
Main Authors: Ye, Xin-Shan, Wong, Chi-Huey
Format: Article
Language:English
Subjects:
Carbohydrate Sequence
Catalysis
Hydroxyl Radical
Magnetic Resonance Spectroscopy
Molecular Sequence Data
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
Thioglycosides - chemistry
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Summary:The assembly of an oligosaccharide library has been achieved in a practical and efficient manner employing a one-pot sequential approach. With the help of the anomeric reactivity values of thioglycosides, using a thioglycoside (mono- or disaccharide) with one free hydroxyl group as acceptor and donor coupled with another fully protected thioglycoside, a di- or trisaccharide is selectively formed without self-condensation and subsequently reacted in situ with an anomerically inactive glycoside (mono- or disaccharide) to form a tri- or tetrasaccharide in high overall yield. The approach enables the rapid assembly of 33 linear or branched fully protected oligosaccharides using designed building blocks. These fully protected oligosaccharides have been partially or completely deprotected to create 29 more structures to further increase the diversity of the library.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo991558w