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
- 1 January 1992
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1992 (1/2) , 196-200
- https://doi.org/10.1055/s-1992-34166
Abstract
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.Keywords
This publication has 0 references indexed in Scilit: