Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine

Dey, Supriya and Jayaraman, Narayanaswamy (2012) Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine. In: Beilstein Journal of Organic Chemistry, 8 . pp. 522-527.

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Abstract

This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a common bromo-oxepine intermediate, involving C-C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals, displayed a good reactivity towards several acceptor moieties in C-C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and Sonogashira coupling reactions afforded 2-deoxy-2-C-alkenyl and -alkynyl derivatives, respectively, the Suzuki reaction afforded 2-deoxy-2-C-aryl septanosides. Deprotection and reduction of the 2-deoxy-2-alkenyl derivative afforded the corresponding 2-deoxy-2-C-alkyl septanoside free of protecting groups. The present study illustrates the reactivity of bromo-oxepine in the synthesis of hitherto unknown septanosides, branching out at C-2, through C-C bond formation with alkyl and aryl substituents.

Item Type:	Journal Article
Publication:	Beilstein Journal of Organic Chemistry
Publisher:	Beilstein Institut.
Additional Information:	Copyright of this article is belongs to Beilstein Institut.
Keywords:	C-C bond formations;2-deoxy sugars;organometallic reactions; septanosides;unsaturated sugars
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	22 Aug 2012 05:02
Last Modified:	22 Aug 2012 05:02
URI:	http://eprints.iisc.ac.in/id/eprint/44467

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