Allylic Strain as a Stereocontrol Element in the Hydrogenation of 3-Hydroxymethyl-cyclohex-3-en-1,2,5-triol Derivatives. Synthesis of the Carbasugar Pseudo-2-deoxy-α-D-glucopyranose.

ABSTRACT: By adaptation of a literature method developed in the glucose series and standard protecting group manipulations a 2-deoxy-D-glucose derivative is converted to a series of 1R,2R,5R-3-hydroxymethyl-cyclohexen-1,2,5-triol derivatives whose reduction to the corresponding diastereomeric D-gluco and L-ido-2-deoxy carbasugars is studied. When the hydroxymethyl group is tied up in a cyclic isopropylidene acetal with the adjacent 6-hydroxy group the cis-fused products with the ido-configuration are formed preferentially whereas protection of the hydroxymethyl group as a methoxymethyl ether results in the formation of the D-gluco isomer on hydrogenation over Raney nickel. This result is rationalized in terms of the minimization of allylic strain in the course of the redu

SUBMITTER: Wen P 

PROVIDER: S-EPMC6261501 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature