Document Detail

A new synthesis of 6-O-acylsucroses and of mixed 6,6'-di-O-acylsucroses.
MedLine Citation:
PMID:  7773988     Owner:  NLM     Status:  MEDLINE    
Various 6-O-acylsucroses were synthesized in good yields from unprotected sucrose in N,N-dimethylformamide and the appropriate 3-acylthiazolidine-2-thiones 6 or 3-acyl-5-methyl-1,3,4-thiadiazole-2(3H)-thiones 7. A selective ionization of the free sugar by sodium hydride or triethylamine, followed by acylation with 6, gave 2-O-acylsucroses which were subjected in situ to intramolecular isomerizations using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or an aqueous solution of triethylamine to yield 6-O-acylsucroses. The later were otherwise obtained directly when sucrose was acylated with 6 or 7 in the presence of DBU. Moreover, mixed 6,6'-di-O-acylsucroses were readily obtained from 6'-monoacylates by using a Mitsunobu reaction without involving the concomitant formation of the 3',4'-epoxide.
K Baczko; C Nugier-Chauvin; J Banoub; P Thibault; D Plusquellec
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Carbohydrate research     Volume:  269     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  1995 Apr 
Date Detail:
Created Date:  1995-07-10     Completed Date:  1995-07-10     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  79-88     Citation Subset:  IM    
Laboratoire de Synthèses et Activations de Biomolécules, associé au CNRS, Ecole Nationale Supérieure de Chimie, Rennes, France.
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MeSH Terms
Carbohydrate Sequence
Disaccharides / chemical synthesis*,  chemistry
Molecular Sequence Data
Sucrose / chemistry*,  metabolism
Reg. No./Substance:
0/Disaccharides; 57-50-1/Sucrose

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