Document Detail


Glycosidation-anomerisation reactions of 6,1-anhydroglucopyranuronic acid and anomerisation of beta-D-glucopyranosiduronic acids promoted by SnCl(4).
MedLine Citation:
PMID:  17086575     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The reaction of silylated nucleophiles with 6,1-anhydroglucopyranuronic acid (glucuronic acid 6,1-lactones) catalysed by tin(IV) chloride provides 1,2-trans or 1,2-cis (deoxy)glycosides in a manner dependent on the donor structure. The alpha-glycoside was obtained for reactions of the donor with the 2-acyl group and 2-deoxydonors, whereas the 2-deoxy-2-iodo donor gave the beta-glycoside. Experimental evidence shows that when 1,2-cis-glycoside formation occurs, the anomerisation of initially formed 1,2-trans-glycosides catalysed by SnCl(4) is possible. The anomerisation of beta-D-glucopyranosiduronic acids was found to be faster, in some cases, than anomerisation of related beta-D-glucopyranosiduronic acid esters and beta-D-glucopyranoside derivatives and the rates are dependent on the structure of the aglycon. Moreover, the rates of anomerisation of beta-D-glucopyranuronic acid derivatives can be qualitatively correlated with rates of hydrolysis of beta-D-glucopyranosiduronic acids. Mechanistic possibilities for the reactions are considered.
Authors:
Colin O'Brien; Monika Poláková; Nigel Pitt; Manuela Tosin; Paul V Murphy
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  13     ISSN:  0947-6539     ISO Abbreviation:  Chemistry     Publication Date:  2007  
Date Detail:
Created Date:  2007-01-09     Completed Date:  2007-03-26     Revised Date:  2009-08-04    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  902-9     Citation Subset:  IM    
Affiliation:
Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Dublin 4, Ireland.
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MeSH Terms
Descriptor/Qualifier:
Glycosylation
Molecular Structure
Monosaccharides / chemical synthesis*,  chemistry
Stereoisomerism
Time Factors
Tin Compounds / chemistry*
Uronic Acids / chemical synthesis*,  chemistry
Chemical
Reg. No./Substance:
0/6,1-anhydroglucopyranuronic acid; 0/Monosaccharides; 0/Tin Compounds; 0/Uronic Acids; 7646-78-8/stannic chloride

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