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Synthesis of Chiral Oxepanes and Pyrans by 3-O-Allylcarbohydrate Nitrone Cycloaddition (3-OACNC)

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Title Synthesis of Chiral Oxepanes and Pyrans by 3-O-Allylcarbohydrate Nitrone Cycloaddition (3-OACNC)
 
Creator Bhattacharjee, Ashoke
Datta, Seema
Chattopadhyay, Partha
Ghoshal, Nanda
Kundu, Asish P
Pal, Arani
Mukhopadhyay, Ranjan
Chowdhury, Sandip
Bhattacharjya, Anup
Patra, Amarendra
 
Subject Chemistry
Structural Biology & Bioinformatics
 
Description 3-O-Allylcarbohydrate nitrone cycloaddition (3-OACNC) furnished pyran and oxepane derivatives from 3-O-allyl hexose
N-benzyl nitrones and 3-O-allyl furanoside-5-aldehyde N-benzyl/methyl nitrones. The regioselectivity of 3-OACNC was found to depend on
the following factors (a) the structural nature of the nitrone (b) substitution and stereochemistry at 3-C of the carbohydrate backbone (c)
substitution at the terminus of the O-allyl moiety. Oxepanes or pyrans obtained from a particular set of a hexose nitrone and the
corresponding furanoside nitrone were converted to enantiomeric cyclic ethers through degradation. A mixture of an oxepane and a pyran
was formed in the intramolecular oxime olefin cycloaddition (IOOC) of a 3-O-allylcarbohydrate derived oxime. q 2003 Elsevier Science
 
Date 2003
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/1197/1/52_TETRAHEDRON_2003.pdf
Bhattacharjee, Ashoke and Datta, Seema and Chattopadhyay, Partha and Ghoshal, Nanda and Kundu, Asish P and Pal, Arani and Mukhopadhyay, Ranjan and Chowdhury, Sandip and Bhattacharjya, Anup and Patra, Amarendra (2003) Synthesis of Chiral Oxepanes and Pyrans by 3-O-Allylcarbohydrate Nitrone Cycloaddition (3-OACNC). Tetrahedron, 59 (25). pp. 4623-4639.
 
Relation http://dx.doi.org/10.1016/S0040-4020(03)00634-3
http://www.eprints.iicb.res.in/1197/