Asymmetric synthesis of carbohydrates: Synthesis of 2-deoxy-D- and 2-deoxy-L-xylofuranosides from a simple achiral precursor

Article abstract of DOI:10.1016/S0040-4039(00)73487-3

The acetylenic alcohol, 3, readily prepared in two steps from propargyl bromide, 1, is converted to methyl 2-deoxy-D-xylofuranoside, 13, and to the unnatural L-enantiomer, 12, in 5 steps and 50% overall yield, utilizing asymmetric dihydroxylation (AD) of alkene 7 for introduction of chirality. A similar strategy from the isomeric Z-allylic alcohol, 4, afforded the 2-deoxy-L-ribofuranoside, but in modest enantiomeric excess.