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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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 |
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Publication: | Journal of Organic Chemistry |
Publisher: | American Chemical Society |
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.ac.in/id/eprint/44159 |
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