Intramolecular Nitrone Cycloaddition Reaction on Carbohydrate-Based Precursors: Application in the Synthesis of Spironucleosides and Spirobisnucleosides
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
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Title |
Intramolecular Nitrone Cycloaddition
Reaction on Carbohydrate-Based
Precursors: Application in the Synthesis of
Spironucleosides and Spirobisnucleosides
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Creator |
Singha, Kaushik
Roy, Atanu Dutta, Pradeep K Tripathi, Subhankar Sahabuddin, Sk Achari, Basudeb Mandal, Sukhendu B |
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Subject |
Chemistry
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Description |
A simple synthesis of chiral spironucleosides and
spirobisnucleosides is described. Intramolecular 1,3-dipolar
nitrone cycloaddition reaction of D-glucose-derived precursors
having olefin at C-3 and nitrone at C-5, C-1, or C-2 (in
nor-series) furnished bisisoxazolidinospirocycles 4-7, 11,
and 12 in good yields. Reductive ring opening of the
isoxazolidine moieties in 4-6 followed by construction of a
nucleoside base upon the generated amino groups smoothly
yielded spirobisnucleosides 17 and 18 and spironucleosides
20 and 21.
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Date |
2004
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Type |
Article
PeerReviewed |
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Format |
application/pdf
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Identifier |
http://www.eprints.iicb.res.in/444/1/JOURNAL_OF_ORGANIC_CHEMISTRY%2C_69(_19)%2C__6507%2D6510_[21].pdf
Singha, Kaushik and Roy, Atanu and Dutta, Pradeep K and Tripathi, Subhankar and Sahabuddin, Sk and Achari, Basudeb and Mandal, Sukhendu B (2004) Intramolecular Nitrone Cycloaddition Reaction on Carbohydrate-Based Precursors: Application in the Synthesis of Spironucleosides and Spirobisnucleosides. Journal of Organic Chemistry, 69 (19). pp. 6507-6510. |
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Relation |
http://dx.doi.org/10.1021/jo035813v
http://www.eprints.iicb.res.in/444/ |
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