Studies on the Oxidation of Methyl 2,3-O-Isopropylidene-beta-D-ribofuranoside with Pyridinium Dichromate. Identification of Unexpected By-Products.

1 January 1990

journal article
research article
Published by Danish Chemical Society in Acta Chemica Scandinavica

Vol. 44 (1) , 90-95
https://doi.org/10.3891/acta.chem.scand.44-0090

Abstract

Oxidation of methyl 2,3-O-isopropylidene-.beta.-D-ribofuranoside (1a) with pyridinum dichromate yields, in addition to the expected methyl 2,3-O-isopropylidene-.beta.-D-ribo-1,4-pentodialdofuranoside (1b), methyl 2,3-O-isopropopylidene-.beta.-D-erythrosidurono-1,4-lactone (3) and the dimeric ester 1e. The structures of the latter compounds were determined by spectroscopic methods. A mechanistic scheme is proposed for their formation.

This publication has 1 reference indexed in Scilit:

Addition of 1-nitroalkanes to methyl 2,3-O-isopropylidene-β-d-ribo-pentodialdo-1,4-furanoside and N6-benzoyl-2′,3′-O-isopropylideneadenosine-5′-aldehyde
Carbohydrate Research, 1983