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Synthesis of Septanosides through an Oxyglycal Route

Ganesh, Vijaya N and Jayaraman, N (2007) Synthesis of Septanosides through an Oxyglycal Route. In: Journal of Organic Chemistry, 72 (15). pp. 5500-5504.

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A new route to synthesize septanoside derivatives from protected 2-hydroxyglycals is reported. Ring expansion of a pyranoside to a septanoside was achieved through key reactions of a cyclopropanation, ring opening, oxidation, and reduction. Methyl septanoside derivatives, namely, methyl \alpha-D-glycero-Dtalo- septanoside and methyl \alpha-D-glycero-L-altro-septanoside, were synthesized in an overall yield of 35% and 46%, respectively, from the corresponding protected 2-hydroxy glycals.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
Publisher: American Chemical Society(ACS)
Additional Information: Copyright of this article belongs to American Chemical Society(ACS).
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 11 Oct 2007
Last Modified: 19 Sep 2010 04:39
URI: http://eprints.iisc.ac.in/id/eprint/11862

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