New chirons from D-glucose. Regio- and diastereoselective C-C bond-forming reactions exploiting novel aldotetrofuranose acetates as chiral synthetic equivalents of tartaric aldehydes

Dhavale, Dilip D. ; Tagliavini, Emilio ; Trombini, Claudio ; Umani-Ronchi, Achille (1989) New chirons from D-glucose. Regio- and diastereoselective C-C bond-forming reactions exploiting novel aldotetrofuranose acetates as chiral synthetic equivalents of tartaric aldehydes Journal of Organic Chemistry, 54 (17). pp. 4100-4105. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo00278a022

Related URL: http://dx.doi.org/10.1021/jo00278a022

Abstract

Two differentially protected tetrafuranose axerates 5 and 6 have beenn prepared from diacetone D-gluccee in parallell short, routes. They clearly act as chiral synthetic equivalents of D- and tartaric aldehyde when exploited in Lewia acid promoted reactions with silicon-bases nucleophiles. The synthesis of immediate precursors of 2-deoxy-L-hexoses is presented as an application.

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