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Synthesis of chiral oxepanes and pyrans by 3-O-allylcarbohydrate nitrone cycloaddition (3-OACNC)
A BHATTACHARJEE, S DATTA, P CHATTOPADHYAY, N GHOSHAL, A P KUNDU, A PAL, R MUKHOPADHYAY, S CHOWDHURY, A BHATTACHARJYA, A PATRA
Published in Elsevier Ltd
2003
Volume: 59
   
Issue: 25
Pages: 4623 - 4639
Abstract
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. © 2003 Elsevier Science Ltd. All rights reserved.
About the journal
JournalData powered by TypesetTetrahedron
PublisherData powered by TypesetElsevier Ltd
ISSN0040-4020