A mild and convenient indium(III) chloride-catalyzed synthesis of thioglycosides

NIS/H2SO4–Silica: a mild and efficient reagent system for the hydrolysis of thioglycosides

“…Column chromatography using n-hexane-EtOAc (3:1) yielded compound 20 (540 mg, 88%) as colourless oil. 1 The reaction was quenched after 30 min. Column chromatography using n-hexane-EtOAc (3:1) yielded compound 24 (404 mg, 93%) as colourless oil.…”

“…Column chromatography using n-hexane-EtOAc (3:1) yielded compound 24 (404 mg, 93%) as colourless oil. 1 …”

“…Column chromatography using n-hexane-EtOAc (3:1) yielded compound 28 (320 mg, 86%) as foam. 1 1.11. Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D D-glucopyranosyl-(1!4)-2,3-O-isopropylidene-1-thio-a-L L-rhamnopyranoside (37)…”

“…[1][2][3] Compatibility of thioglycosides with many protecting groups allows the protecting group manipulations that are required during oligosaccharide synthesis. 3,4 Hence they are often used as glycosyl donors for the synthesis of oligosaccharides and glycoconjugates.…”

Using In(III) as a promoter for glycosylation

“…15 In carbohydrate synthesis, In(III) has been reported to catalyze peracetylation, 16 acetolysis, formation and hydrolysis of acetals, and formation of thioglycosides. 17,18 In addition, InCl 3 has been reported as a glycosylation promoter using glycohalide donors, 19,20 as well as peracetylated trichloroacetimidates. 21 While these sources focused on InCl 3 , this paper broadens the scope to include other In(III) glycosylation promoters in the presence of a variety of protecting groups and alcohol acceptors.…”