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