Synthesis and Intramolecular Nitrile Oxide Cycloaddition of 3,5¢-Ether-Linked Pseudooligosaccharide Derivatives: An Approach to Chiral Macrooxacycles
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| 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/ |
|