Synthesis of 1,2,3-tri-O-acetyl-5-deoxy-d-ribofuranose from d-ribose Original Research Article

A practical route towards the synthesis of 1,2,3-tri-O-acetyl-5-deoxy-d-ribofuranose from d-ribose is described. The key steps include deoxygenation of methyl 2,3-O-isopropylidene-5-O-sulfonyloxy-β-d-ribofuranoside by reductive displacement employing hydride reagents. Subsequent total hydrolysis followed by acetylation led to the title compound in 56% overall yield from d-ribose. The sequence is simple, inexpensive, high yielding and clearly suitable for multi-gram preparations.