Synthesis of 2-Propynyl 2-Acetamido-sss3,4,6-Tri-O-Acetyl-2-Deoxy-1-Thio-β-d-Glucopyranoside, 2-Propynyl 3,4,6-Tri-O-Acetyl-2-Deoxy-2-Phthalimido-1-Thio-β-d-Glucopyranoside and Their 2-(2-Propynylox­yethoxy)ethyl Analogs

Abstract

The popular CuAAC (Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition), also referred to as the click reaction, has been adopted by carbohydrate chemists for the construction of neoglycoconjugates. Thus, the synthesis of alkynyl- and azide-sugar precursors through readily available and high-yielding methods has become an important topic. One option for the synthesis of neoglycoconjugates is to employ thiosugars as recognition elements, which are more flexible isostericstructures than the naturally occurring O-glycosides. Still, they are recognized by carbohydrate-binding proteins without the loss of affinity, with the advantage of their increased resistance to hydrolysis.