Abstract
The first synthesis of 2,3,4-tri-O-benzyl-5-thio-d-ribono-1,5-lactone was achieved, in five steps, from 5-bromo-5-deoxy-d-ribono-1,4-lactone; displacement of the bromide group, in methyl 2,3,4-tri-O-benzyl-5-bromo-5-deoxy-d-ribonate (7), gave methyl 2,3,4-tri-O-benzyl-5-S-acetyl-5-thio-d-ribonate (10) in 96% yield. Saponification of compound 10 gave the methyl 2,3,4-tri-O-benzyl-5-thio-d-ribonic acid (11) in 98% yield. Treatment of 11 with DIC-HOBt as coupling reagents led, after cyclisation, the target compound, 2,3,4-tri-O-benzyl-5-thio-d-ribono-1,5-lactone (12) in 75% yield.
Key words
d-ribono-1,4-lactone - methyl 5-bromo-5-deoxy-d-ribonate - DIC-HOBt - 2,3,4-tri-O-benzyl-5-thio-d-ribono-1,5-lactone
