Synthesis of 2-Propynyl 2-Acetamido-3,4,6-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

ALEJANDRO E. CRISTÓFALO; HUGO O. MONTENEGRO; MARÍA EMILIA CANO; MARÍA LAURA UHRIG; JUAN PABLO COLOMER; CHRISTIAN VOGEL; PAUL V. MURPHY; TANJA WRODNIGG

Carbohydrate Chemistry: Proven Synthetic Methods, Volume 5

CRC Press Taylor & Francis Group

Año: 2020;

The synthesis of alkynyl- and azide-sugar precursors for their use in the click reaction 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 isosteric structures than the naturally occurring O-glycosides. Still, they are recognized by carbohydrate-binding proteins without loss of affinity, with the advantage of their increased resistance to hydrolysis.This work, we describe the synthesis of precursors of alkynyl-functionalized β-N-protected thioglucosamine by a one-pot procedure starting from either N-acetyl or N-phthaloyl glucosamine peracetates