Document Detail

Direct Synthesis of Maradolipids and Other Trehalose 6-Monoesters and 6,6'-Diesters.
MedLine Citation:
PMID:  23227969     Owner:  NLM     Status:  Publisher    
It was shown that reaction of trehalose with one equivalent of a fatty acid in pyridine promoted by one equivalent of the uronium-based coupling agent TBTU at room temperature gives a good yield of the primary ester accompanied by small amounts of the diprimary ester, using hexanoic, palmitic, and oleic acids as examples. Reactions using two equivalents of the fatty acids gave the symmetrical diesters. The monoesters can be reacted with different fatty acids to give non-symmetric 6,6'-diesters in very good yields. Compounds synthesized include the most abundant component of the very complex maradolipid mixture, 6-O-(13-methyltetradecanoyl)-6'-O-oleoyltrehalose, and a component potentially present in this mixture, 6-O-(12-methyltetradecanoyl)-6'-O-oleoyltrehalose, a derivative of an ante fatty acid. The C5-C6 rotameric populations of 6-O-monoesters, symmetrical 6,6'-diesters, and 2,6,6'-triesters of fatty acids were calculated from the values of the H5-H6R and H5-H6S coupling constants and found to be similar to those found for glucose. The rotameric population of the monosubstituted glucose residue in the 2,6,6'-triesters was altered considerably to favor the gt rotamer, presumably because of attraction between the 2- and 6'-fatty acid chains.
Nawal K Paul; Jean-d'Amour Karemerwa Twibanire; T Bruce Grindley
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-12-10
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Dec 
Date Detail:
Created Date:  2012-12-11     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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