Highly efficient synthesis of 1-thioglycosides in solution and solid phase using iminophosphorane bases.
Disaccharides of 1-thioglycosides, an important class of glycomimics, can be synthesized by direct S-alkylation in exceptionally high yields when iminophosphorane bases are employed. The reaction conditions employed appear to be general and stereospecific. Axial and equatorial 4-triflates and primary tosylates of alkyl pyranosides provided excellent yields of thio-disaccharides without substantial elimination products. The iminophosphorane bases also proved to be useful in solid support-bound couplings of thioglycosides though with lower efficiency.
Xu
W
W
The Department of Chemistry and Biochemistry, University of Delaware, Newark 19716, USA.
Springfield
S A
SA
Koh
J T
JT
D000478:Alkylation; D002851:Chromatography, High Pressure Liquid; D010753:Phosphoranes / Q000737:chemistry*; D013865:Thioglycosides / Q000138:chemical synthesis*
D010753:Phosphoranes; D013865:Thioglycosides