Chemoselective activation of ethyl vs. phenyl thioglycosides: one-pot synthesis of oligosaccharides

Abstract

Ethyl and phenyl thioglycosides are the two most common types of thioglycoside donors in carbohydragte chemistry, however, chemoselective activation of ethyl vs phenyl thioglycosides is very rare in the literature....

Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH4

“…Following general process A, starting from 6a (100 mg, 0.232 mmol), after 0.5 h of ring-opening reaction for the crude anhydro sugar, purification by silica gel flash column chromatography afforded 6 as a colorless oil (81.5 mg, 63%). Rf = 0.36 (petroleum ether/ethyl acetate 6:1); 1 Phenyl 3,4,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside (7). Following general process A, starting from 7a (100 mg, 0.218 mmol), after 20 min of ring-opening reaction for the crude anhydro sugar, purification by silica gel flash column chromatography afforded 7 as colorless syrup (81.6 mg, 64%).…”

“…The chemical synthesis of complex carbohydrates is an important research topic in carbohydrate chemistry due to their crucial roles in biological processes [1][2][3][4][5]. Thioglycoside donors are widely used in these syntheses due to their advantages, such as easy preparation, stable chemical properties, and various activation methods [6][7][8][9][10][11][12]. Generally, each glycosylation reaction between the donor and acceptor may produce a product in the α or β configuration, which will lead to adverse effects, such as reduced yield and difficult purification.…”