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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
 
Creator Singha, Kaushik
Roy, Atanu
Dutta, Pradeep K
Tripathi, Subhankar
Sahabuddin, Sk
Achari, Basudeb
Mandal, Sukhendu B
 
Subject Chemistry
 
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.
 
Date 2004
 
Type Article
PeerReviewed
 
Format application/pdf
 
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.
 
Relation http://dx.doi.org/10.1021/jo035813v
http://www.eprints.iicb.res.in/444/