Synthesis of 1, 2, 3-tri-O-acetyl-5-deoxy-D-ribofuranose from D-ribose

P Sairam, R Puranik, BS Rao, PV Swamy…

Index: Sairam, Pothukuchi; Puranik, Ramachandra; Sreenivasa Rao, Bhatraju; Veerabhadra Swamy, Ponnapalli; Chandra, Sharad Carbohydrate Research, 2003 , vol. 338, # 4 p. 303 - 306

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Citation Number: 28

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-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 ...

~87%

~72%

~71%

~44%

~94%

~78%

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