Document Detail


Iodine-hexamethyldisilane (HMDS)-mediated anomerization of peracetylated 1,2-trans-linked alkyl and aryl glycosides.
MedLine Citation:
PMID:  20304387     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Treatment of peracetylated alkyl and aryl 1,2-trans-glycosides with iodine in the presence of HMDS has been found to result in the anomerization leading to the formation of the respective 1,2-cis-glycosides. In the case of alkyl glycosides with aglycons of short alkyl chain length complete anomerization to the alpha-glycosides was observed while with those of longer chain length the process was found to be incomplete. The observations have been interpreted mechanistically.
Authors:
Satish Malik; Krupesh J Shah; K P Ravindranathan Kartha
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-02-19
Journal Detail:
Title:  Carbohydrate research     Volume:  345     ISSN:  1873-426X     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2010 May 
Date Detail:
Created Date:  2010-04-19     Completed Date:  2010-07-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  867-71     Citation Subset:  IM    
Affiliation:
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Punjab, India.
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MeSH Terms
Descriptor/Qualifier:
Acetylation
Glycosides / chemistry*
Indicators and Reagents / chemistry
Iodine / chemistry*
Oxygen / chemistry
Silanes / chemistry*
Stereoisomerism
Chemical
Reg. No./Substance:
0/Glycosides; 0/Indicators and Reagents; 0/Silanes; 0/hexamethyldisilane; 7553-56-2/Iodine; 7782-44-7/Oxygen

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


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