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Iodine-sodium cyanoborohydride-mediated reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides.
MedLine Citation:
PMID:  21055729     Owner:  NLM     Status:  In-Process    
Abstract/OtherAbstract:
A quick, efficient and convenient method for the regiospecific reductive ring opening of 4,6-O-benzylidene acetals of O-/S-alkyl/aryl glycosides of mono- and disaccharides, leading to the exclusive formation of the corresponding 6-O-benzyl ethers, using sodium cyanoborohydride in the presence of molecular iodine, is reported. It has been observed that common protecting groups such as ethers and esters are well tolerated under the conditions studied. The reaction was proved unsuccessful when applied to a glucosamine-derived benzylidene acetal.
Authors:
Kaki Venkata Rao; Premanand R Patil; Sridhar Atmakuri; K P Ravindranathan Kartha
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-10-20
Journal Detail:
Title:  Carbohydrate research     Volume:  345     ISSN:  1873-426X     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2010 Dec 
Date Detail:
Created Date:  2010-11-24     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  2709-13     Citation Subset:  IM    
Copyright Information:
Copyright © 2010 Elsevier Ltd. All rights reserved.
Affiliation:
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, S.A.S. Nagar, Punjab, India.
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