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Synthesis of 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose from D-ribose
Pothukuchi Sairam1, Ramachandra Puranik, Bhatraju Sreenivasa Rao
1Critical Care Division, Dr Reddy's Laboratories Ltd., IDA Bollaram, Andhra Pradesh 500 016, Hyderabad, India. sairam@drreddys.com
Carbohydrate Research
|February 1, 2003
Abstract:
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-beta-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.