An efficient route to thioglycosides with the 2,3-anhydro-D-ribo stereochemistry.
An improved route for the synthesis of p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-beta-D-ribofuranoside and its alpha anomer, which are important intermediates in the synthesis of alpha- and beta-D-arabinofuranosides, has been developed. The products are obtained in six steps from D-xylose in 39% overall yield.
Tilekar
Jayant N
JN
Department of Chemistry and Alberta Ingenuity Centre for Carbohydrate Science, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, AB, Canada T6G 2G2.
Lowary
Todd L
TL
D008722:Methods; D008968:Molecular Conformation; D013865:Thioglycosides / Q000138:chemical synthesis*; D014994:Xylose / Q000737:chemistry
C500615:4-tolyl 2,3-anhydro-5-O-benzoyl-1-thioribofuranoside; D013865:Thioglycosides; D014994:Xylose