Document Detail


Polymer-supported tin carbohydrate chemistry.
MedLine Citation:
PMID:  9530959     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
It was anticipated that stannylation of carbohydrates could be achieved using tin on a polymer-support. Such immobilization simplifies the purification of the carbohydrate because the toxic tin reagent can be removed by filtration. In this case an alkene linker (3-buten-1-ol) was added to chloromethylated 2% cross-linked polystyrene by etherification. Photochemical hydrostannylation with dibutyltinchlorohydride gave a polymer bound trialkyl tin chloride. The Sn-Cl could be hydrolysed with NaOH to yield a resin with terminal Sn-O bonds. Highly regioselective acylation of methyl alpha-D-mannopyranoside (alphaMeMan) to its 3-O-benzoyl derivative was achieved. Traces of the mono 6-O-benzoate and the 3,6-di-O-benzoate were also obtained. Methyl alpha-D-glucopyranoside was also selectively acylated to its 2-O-benzoate but this reaction gave a more complex mixture. The isolated yields (10-30% based on sugar) were disappointingly low. The yields were improved to about 60% with 5% cross-linked resin.
Authors:
D M Whitfield; T Ogawa
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Glycoconjugate journal     Volume:  15     ISSN:  0282-0080     ISO Abbreviation:  Glycoconj. J.     Publication Date:  1998 Jan 
Date Detail:
Created Date:  1998-05-06     Completed Date:  1998-05-06     Revised Date:  2000-12-18    
Medline Journal Info:
Nlm Unique ID:  8603310     Medline TA:  Glycoconj J     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  75-8     Citation Subset:  IM    
Affiliation:
National Research Council, Ottawa, Ontario, Canada.
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MeSH Terms
Descriptor/Qualifier:
Acylation
Carbohydrates / chemistry*
Monosaccharides / chemistry
Polymers
Tin / chemistry
Chemical
Reg. No./Substance:
0/Carbohydrates; 0/Monosaccharides; 0/Polymers; 7440-31-5/Tin

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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