Novel stereocontrolled amidoglycosylation of alcohols with acetylated glycals and sulfamate ester
A regio- and stereo-controlled, one-pot amidoglycosylation of alcohols has been achieved using O-acetylated glycals, trichloroethoxysulfonamide, and iodosobenzene in the presence of a rhodium(ii) catalyst. The reaction would proceed via stereoselective intermolecular aziridination of the glycal. This journal is the Partner Organisations 2014.
Convenient stereocontrolled amidoglycosylation of alcohols with acetylated glycals and trichloroethoxysulfonamide
A regio- and stereo-controlled, rhodium(II)-catalyzed amidoglycosylation of alcohols has been developed using O-acetylated glycals, trichloroethoxysulfonamide, and iodosobenzene. This one-pot amidoglycosylation was applied to a variety of primary and secondary alcohols to afford the β-O-glycosides with acceptable yields up to 84%. The reaction would proceed via stereoselective intermolecular aziridination of the glycal from the α-face followed by SN2 reaction with alcohol at C-1 from the β-face to give 1,2:2,3-di-trans-substituted isomer only.
Synthesis and surface-active properties of some alkyl 2-amino-2-deoxy-β-D-glucopyranosides
Several alkyl 2-acetamido-2-deoxy-β-D-glucopyranosides were synthesized using either the oxazoline or the N-allyloxycarbonyl procedure.The latter procedure gave better yields with fatty alcohols and cholesterol.The derivatives thus prepared were partly of fully deprotected and their surface-active properties assessed.Keywords: 2-Amino-2-deoxy-D-glucose; Amphiphiles; Surfactant; 14C-labelled