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Synthesis of 2-Deoxy-2-C-alkyl Glycal and Glycopyranosides from 2-Hydroxy Glycal Ester

Daskhan, Gour Chand and Jayaraman, Narayanaswamy (2012) Synthesis of 2-Deoxy-2-C-alkyl Glycal and Glycopyranosides from 2-Hydroxy Glycal Ester. In: Journal of Organic Chemistry, 77 (5). pp. 2185-2191.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo202240f

Abstract

A method to convert 2-hydroxy glycol ester to the corresponding corresponding 2-deoxy-2-C-alkyl glycol in a facile manner, through key reactions including (i) C-allylation at C-1, (ii) Wittig reaction, and (iii) Cope rearrangement of a 1,5-diene derivative, is reported. The alpha-anomer of the 1,5-diene derivative underwent Cope rearrangement to afford 2-deoxy-2-C-glycal derivative, whereas the beta-anomer was found to be unreactive. Employing this sequence, was transformed to 3,4,6-tri-O-benzyl-2-deoxy-2-C-alkyl-1,5-anhydro-D-arabino-hex-1-enitol. 2-Deoxy-2-C-alkyl glycol derivative is a suitable glycosyl donor to prepare 2-deoxy-2-C-alkyl glycosides, mediated through haloglycosylation and a subsequent dehalogenation. A number of 2-deoxy-2-C-alkyl glycosides, with both glycosyl and nonglycosyl moieties at the reducing end, are thus prepared from the glycol.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 10 Apr 2012 09:58
Last Modified: 10 Apr 2012 09:58
URI: http://eprints.iisc.ernet.in/id/eprint/44159

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