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Synthesis and Intramolecular Nitrile Oxide Cycloaddition of 3,5¢-Ether-Linked Pseudooligosaccharide Derivatives: An Approach to Chiral Macrooxacycles

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Title Synthesis and Intramolecular Nitrile Oxide
Cycloaddition of 3,5¢-Ether-Linked
Pseudooligosaccharide Derivatives: An
Approach to Chiral Macrooxacycles
 
Creator Sengupta, Jhimli
Mukhopadhyay, Ranjan
Bhattacharjya, Anup
Bhadbhade, Mohan M
Bhosekar, Gaurav V
 
Subject Chemistry
 
Description 3,5¢-Ether-linked pseudooligopentose derivatives were synthesized
for the first time from readily available carbohydrate
precursors. The 1,2-isopropylidene-protected etherlinked
oligopentoses are potentially important as precursors
of novel RNA analogues. Intramolecular cycloaddition of the
nitrile oxides prepared from these derivatives led to the
diastereoselective formation of chiral isoxazolines fused to
10-16-membered oxacycles. The stereochemistry of some of
these isoxazolines was established by X-ray diffraction and
NOESY analysis.
 
Publisher American Chemical Society
 
Date 2005
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/327/1/JOURNAL_OF_ORGANIC_CHEMISTRY_70(_21_)_8579%2D85822005[11].pdf
Sengupta, Jhimli and Mukhopadhyay, Ranjan and Bhattacharjya, Anup and Bhadbhade, Mohan M and Bhosekar, Gaurav V (2005) Synthesis and Intramolecular Nitrile Oxide Cycloaddition of 3,5¢-Ether-Linked Pseudooligosaccharide Derivatives: An Approach to Chiral Macrooxacycles. The Journal of Organic Chemistry, 70 (21). pp. 8579-8582.
 
Relation http://dx.doi.org/10.1021/jo050689w CCC: $30.25
http://www.eprints.iicb.res.in/327/