Synthesis of 2-C-(4-aminocarbonyl-2-thiazoyl)-1,4-anhydro-L-xylitols and their fluoro derivatives

Article abstract of DOI:10.1016/S0957-4166(97)00615-0

3,5-O-Benzylidene-2-C-cyano-1,4-anhydro-L-xylitol 7 was synthesized stereoselectively from D-xylose in 7 steps, 2-C-(4-Aminocarbonyl-2-thiazoyl)- 1,4-anhydro-L-xylitols and their fluoro derivatives were synthesized from the cyanohydrin 7. Fluorination of compound 9 proceeded with retention of configuration using diethylaminosulfur trifluoride (DAST).