Synthesis of potential inhibitors of glycosyltransferases representing UDP-GlcNAc

Based on rational design of the transition state analog inhibitors of glycosyltransferases, four model glycomimetics of this type, viz. benzyl 2-thio- α - d fructofuranoside 1-diethylphosphate ( XIa ), its β -anomer ( XIb ), and their ethyl 2-thio analogs — α -anomer ( XIIa ) and β -anomer ( XIIb ), were synthesized. In addition, fourteen precursors arising during the synthesis of the desired final model compounds ( XI and XII ), partially or fully acetylated benzyl and/or ethyl 2-thiofructofuranoside 1-diethyl phosphates, were isolated and characterized with the aim to prepare complete series of glycomimetics, representing donor UDP-GlcNAc designated for biological assays on human GnT’s, viz. GnT-I, Core2GnT, and GnT-V.