Organoboron-Catalyzed Regio- and Stereoselective Formation of β‑2-Deoxyglycosidic Linkages

A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-selective pathway by enhancement of acceptor nuc...

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Bibliographic Details
Published in:Organic letters 2014-07, Vol.16 (13), p.3604-3607
Main Authors: Beale, Thomas M, Moon, Patrick J, Taylor, Mark S
Format: Article
Language:English
Subjects:
Borinic Acids - chemistry
Catalysis
Combinatorial Chemistry Techniques
Glycosides - chemical synthesis
Glycosides - chemistry
Glycosylation
Molecular Structure
Stereoisomerism
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Summary:A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-selective pathway by enhancement of acceptor nucleophilicity constitutes a distinct approach from previous work, which has been aimed at modulating donor reactivity by variation of protective and/or leaving groups.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol501711v