Stereochemical studies—XXX : Stereoselective synthesis of D-ribose from L-glutamic acid

A new stereoselective synthesis of D-ribose (14) starting from L-glutamic acid (1) is described, by making use of the chiral center of 1 as that at C-4 of 14. Oxidation of methyl 5-O-benzyl-2,3-dideoxy-D-pent-2-enofuranoside (10) with potassium permanganate or osmium tetroxide was shown to occur preferentially from the rear side of the OMe group at C-1.