Synthèse Du 1‐Azido‐2, 3, 5‐Tri‐O‐Benzoyl‐α‐D‐Lyxofuranose
- 1 January 1960
- journal article
- research article
- Published by Wiley in Bulletin des Sociétés Chimiques Belges
- Vol. 69 (1-2) , 57-62
- https://doi.org/10.1002/bscb.19600690106
Abstract
1‐azido‐2,3,5‐tri‐0‐benzoyl‐α‐D‐lyxofuranose (VII) has been synthetized as follow: perbenzoylation of methyl‐D‐lyxofuranoside (IV m. p. 93‐94°) gives methyl‐2,3,5‐tri‐O‐benzoyl‐D‐lyxofuranoside (V) which is selectively hydrolysed (AcOH sat. with HBr) and acetylated ((Ac)2O + pyridine) to l‐acetyl‐2,3,5‐tri‐O‐benzoyl‐D‐lyxofuranose (VI m. p. 104‐104,5°). This acetate is converted to 1‐azido‐2,3,5‐tri‐O‐benzoyl‐α‐D‐lyxofuranose (VII) by chlorodeacetylation (HCl in ether) followed by azidodechlorination (NaN3 in CH3CN). Work on the condensation of this azidosugar with active methylene compounds is under way.Keywords
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