4-O-Benzyl-2,3-O-isopropylidene-D-erythrose and -D-threose from 2,3-O-Isopropylidene-D-glyceraldehyde via Thiazole Intermediates. Synthesis of 2-Deoxykanosamine

Alessandro Dondoni; Pedro Merino

doi:10.1055/s-1992-34166

Synthesis 1992; 1992(1/2): 196-200
DOI: 10.1055/s-1992-34166

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4-O-Benzyl-2,3-O-isopropylidene-D-erythrose and -D-threose from 2,3-O-Isopropylidene-D-glyceraldehyde via Thiazole Intermediates. Synthesis of 2-Deoxykanosamine

Alessandro Dondoni^* , Pedro Merino

^*Dipartimento di Chimica, Laboratorio di Chimica Organica, Università, Ferrara, Italy

Abstract

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The adduct derived from 2,3-O-isopropylidene-D-glyceraldehyde and 2-(trimethylsilyl)thiazole is readily converted into the title D-erythrose (50% overal yield) by selective protection of the hydroxy groups and cleavage of the thiazole ring; the D-threose derivative is obtained from the former by base-catalyzed epimerization at C-2. Wittig olefination of the D-erythrose derivative followed by Michael addition of benzylamine and aldehyde liberation from the thiazole ring leads to the amino sugar 2-deoxykanosamine (methyl 6-O-benzyl-3-benzylamino-2,3-dideoxy-α -D-arabinopyranoside) in 50% overall yield.

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