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

Synthesis of (1→3) Thiodisaccharides of GlcNAc and the Serendipitous Formation of 2,3-Dideoxy-(1→2)-thiodisaccharides through a Vinyl Azide Intermediate

“…In situ, further peracetylation led efficiently to 15α,β and 13α,β , respectively. These anomeric mixtures constitute alternative building blocks for further conjugation, taking into account that the absence of the benzylidene group makes them also compatible with thioglycosylation methods involving strong Lewis acids, such as BF 3 ·OEt 2 . Moreover, reduction of the azide present in the thiodisaccharides obtained could be effectively achieved by the classical reported procedure using AcSH/pyridine. , …”

“…These anomeric mixtures constitute alternative building blocks for further conjugation, taking into account that the absence of the benzylidene group makes them also compatible with thioglycosylation methods involving strong Lewis acids, such as BF 3 •OEt 2 . 54 Moreover, reduction of the azide present in the thiodisaccharides obtained could be effectively achieved by the classical reported procedure using AcSH/pyridine. 48,49 A relevant finding associated to the S N 2 reaction explored in this work was that vinyl azide 7 was formed by an elimination reaction of triflate 3.…”