A one-pot synthesis of beta-C-glucopyranosides from exo-glucal, p-tolylsulfenyl chloride, an alpha-methoxyalkene, and an external nucleophile.
[formula: see text] beta-C-Glycosides were synthesized in one-pot experiments using the following sequence of four reactions: (i) addition of p-TolSCl to an alpha-methoxyalkene, (ii) generation of the episulfonium ion from a beta-(arylsulfanyl)alkyl chloride, (iii) reaction of the episulfonium intermediate with benzylated exo-D-glucal to form a cyclic five-membered sulfonium salt, and (iv) quenching of the sulfonium salt with the external nucleophile: H2O, CH3OH, or NaCNBH3.
Liu
Hui
H
Chemistry Department, University of North Dakota, Grand Forks, North Dakota 58202-9024, USA.
Smoliakova
Irina P
IP
Koikov
Leonid N
LN
D002125:Calcium Gluconate / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis*; D006027:Glycosides; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis*
C438934:C-glycoside; D005960:Glucosides; D006027:Glycosides; D007202:Indicators and Reagents; D009005:Monosaccharides; D002125:Calcium Gluconate