A facile method for preparation of 3-thio-sugars and 3-thio-glycals. synthesis of 3′-mercapto-3′-deamino-doxorubicin

General method for the preparation of synthetically useful 3-thio-glycals and biologically important 3-thio-sugars is described. The 3-thio-2,3,6-trideoxy-L-hexopyranoses (13, 14) and corresponding 3-S-acetyl-1,5-anhydro-3-thio-L-hex-1-enitols (15-18) were synthesized using 3,4-di-O-acetyl-L-fucal (1) and 3,4-di-O-acetyl-L-rhamnal (2) as substrates. The 3-thio-glycals were successfully employed for the synthesis of 3′-mercapto-3′-deamino-doxorubicin and its analogues.