Diastereofacial selection in the 1,2-addition of MeMgX and MeLi to 4- oxo sugar: Efficient synthesis of 4-C-methyl-1-S-β-D-gluco- and galactopyranoside building blocks of moenomycin

Article abstract of DOI:10.1016/S0040-4039(99)00823-0

The stereochemical course of the 1,2-addition upon treatment of various 1-thio-4-oxo sugars with MeMgX and MeLi has been determined. The effects of reagent, solvent, and neighboring functionalities in the gluco/galacto (non- chelation/chelation controlled