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Synthesis 2004(7): 1083-1087  
DOI: 10.1055/s-2004-822328
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© Georg Thieme Verlag Stuttgart · New York

4-Octulose Derivatives; Part 8:1 Highly Stereocontrolled Synthesis of 2-Deoxy-4-octulosononitriles by Reformatsky-Type Reaction

Isidoro Izquierdo*, María T. Plaza, Juan. A. Tamayo, Antonio J. Mota
Department of Medicinal and Organic Chemistry, Faculty of Pharmacy, University of Granada, 18071 Granada, Spain
Fax: +34(958)243845; e-Mail: isidoro@ugr.es ;
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Publication History

Received 4 February 2004
Publication Date:
02 April 2004 (online)

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Abstract

2-Deoxy-4,5:6,7-di-O-isopropylidene-β-d-manno-oct-4-ulo-4,8-pyranosononitrile (3) and 2-deoxy-4,5:6,8-di-O-isopropylidene-α-l-gulo-oct-4-ulo-4,7-furanosononitrile (5) were prepared by a high stereocontrolled indium-mediated Reformatsky-type reaction of 2,3:4,5-di-O-isopropylidene-β-d-arabino-hexos-2-ulopyranose (1) and 2,3:4,6-di-O-isopropylidene-α-l-xylo-hexos-2-ulofuranose (2) with bromoacetonitrile, repectively. The configurations at C(3) in 3 and 5 were established by chemical correlation.

Key words

d-fructose - l-sorbose - stereoselective synthesis - 2-deoxy-4-octulosononitriles - indium