Syntheses of 4, 5-Di-O-bexzyl-2-deoxy-2-C-methyl L-lyxose and Methyl 4, 5-Di-O-bexzyl-2-deoxy-2-C-methyl-3-O-metkyl-L-lyxonate
Title:
Syntheses of 4, 5-Di-O-bexzyl-2-deoxy-2-C-methyl L-lyxose and Methyl 4, 5-Di-O-bexzyl-2-deoxy-2-C-methyl-3-O-metkyl-L-lyxonate
Author:
Tadano, Kin-Ichi Iimura, Youichi Suami, Tetsuo
Appeared in:
Journal of carbohydrate chemistry
Paging:
Volume 5 (1986) nr. 3 pages 411-422
Year:
1986-09-01
Contents:
The title compounds, which possess C-methyl groups at the α-position of carbonyl groups and vicinal hydroxyl groups with syn (three) relationship, were synthesized efficiently from known 3-decxy-1, 2-O-isopropylidene-3-C-methyl-α-D-allofuranose. The synthetic routes involve: 1) inversion of C-5 configuration of the starting sugar, 2) suitable protection of the 5, 6-diol, and 3) glycol cleavage of the 1, 2-diol to an aldehyde or direct oxidation of the diol to carboxylic acid.