Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions

Abstract

An environmentally friendly and simple sensitized photooxidation methodology to obtain glycosyl sulfoxides with outstanding chemoselectivity in aerobic conditions is described.

Anomeric Thioglycosides Give Different Anomeric Product Distributions under NIS/TfOH Activation

“…Methyl 2,3,4,6-tetra- O -acetyl-1-deoxy-1-thio-β- d -glucopyranoside (2.389 g, 6.313 mmol, 1.0 equiv) was dissolved in anhydrous MeOH (20 mL). NaOMe in MeOH (25 wt %) was added in a dropwise fashion until pH 10 was reached.…”

“…36 1 H NMR (400 MHz, CDCl 10.0 Hz, J 5,6a 3.9 Hz, J 5,6b 2.0 Hz, 1H, H5), 3.95−3.85 (m, 2H, H3, H4), 3.78 (dd, J 6a,6b 10.6 Hz, 1H, H6aa), 3.70−3.63 (m, 2H, H2, H6b), 2.07 (s, 3H, SCH 3 ). 13 37 (2.389 g, 6.313 mmol, 1.0 equiv) was dissolved in anhydrous MeOH (20 mL). NaOMe in MeOH (25 wt %) was added in a dropwise fashion until pH 10 was reached.…”

Solvent free, catalytic and diastereoselective preparation of aryl and alkyl thioglycosides as key components for oligosaccharide synthesis

“…116.0–117.0 °C (EtOH), lit. 116.3–117.9 °C, 25 HRMS (ES): calcd for C 20 H 24 O 9 SNa + m / z 463.1033; found m / z 463.1038.…”