title: Synthesis of 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose from D-ribose.
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.
authors.affiliation: Critical Care Division, Dr Reddy's Laboratories Ltd., IDA Bollaram, Andhra Pradesh 500 016, Hyderabad, India. sairam@drreddys.com
authors.forename: Pothukuchi
authors.initials: P
authors.lastname: Sairam
authors.forename: Ramachandra
authors.initials: R
authors.lastname: Puranik
authors.forename: Bhatraju Sreenivasa
authors.initials: BS
authors.lastname: Rao
authors.forename: Ponnapalli Veerabhadra
authors.initials: PV
authors.lastname: Swamy
authors.forename: Sharad
authors.initials: S
authors.lastname: Chandra
mesh_terms: D000107:Acetylation; D006868:Hydrolysis; D008722:Methods; D009005:Monosaccharides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D012266:Ribose / Q000737:chemistry*
chemical_list: C478185:1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose; D009005:Monosaccharides; D012266:Ribose