THE ABSOLUTE CONFIGURATION OFdextro-1-DEUTERIOETHANOL

Abstract

Reduction of 1,2-O-isopropylidene-3-O-benzyl-5-oxo-α-D-xylofuranose with lithium aluminum deuteride followed by removal of the isopropylidene and benzyl groups provided 5-deuterio-D-xylose. Nuclear magnetic resonance examination of the 5-deuterio-β-D-xylopyranose tetraacetate showed the isomer with the 5-carbon in the R-configuration (deuterium equatorial) to be present in 30% excess. The substance was degraded to 1-deuterioethanol, which possessed a dextrorotation of the magnitude expected and which necessarily possessed the R-configuration. This result confirmed the prediction made by Brewster (Tetrahedron Letters, 20, 23 (1959)).