Synthesis of (6-H-2)- and 6-deoxy-6-fluoro-L-galactose derivatives

Authors
Brackhagen, M Boye, H Vogel, C
Citation
M. Brackhagen et al., Synthesis of (6-H-2)- and 6-deoxy-6-fluoro-L-galactose derivatives, J CARB CHEM, 20(1), 2001, pp. 31-43
Citations number
9
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
ISSN journal
07328303 → ACNP
Volume
20
Issue
1
Year of publication
2001
Pages
31 - 43
Database
ISI
SICI code
0732-8303(2001)20:1<31:SO(A6D>2.0.ZU;2-8
Abstract
The selective oxidation of trimethylsilylated D-galactose diethyl dithioace tal using Collins reagent provided the corresponding D-galacto-hexodialdo d ithioacetal. Successive acid hydrolysis, isopropylidenation, and cleavage o f the dithio acetal group gave the 1,2;3,4-di-O-isopropylidene-L-galacto-he xodialdo-1,5-pyranose as a key intermediate for the synthesis of 6-fluoro- and 6-deutero-substituted L-fucose derivatives.