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Synthesis of 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose from D-ribose. 2003

Pothukuchi Sairam, and Ramachandra Puranik, and Bhatraju Sreenivasa Rao, and Ponnapalli Veerabhadra Swamy, and Sharad Chandra
Critical Care Division, Dr Reddy's Laboratories Ltd., IDA Bollaram, Andhra Pradesh 500 016, Hyderabad, India. sairam@drreddys.com

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.

UI MeSH Term Description Entries
D008722 Methods A series of steps taken in order to conduct research. Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D009005 Monosaccharides Single chain carbohydrates that are the most basic units of CARBOHYDRATES. They are typically colorless crystalline substances with a sweet taste and have the same general formula CnH2nOn. Monosaccharide,Simple Sugar,Simple Sugars,Sugar, Simple,Sugars, Simple
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D006868 Hydrolysis The process of cleaving a chemical compound by the addition of a molecule of water.
D000107 Acetylation Formation of an acetyl derivative. (Stedman, 25th ed) Acetylations
D012266 Ribose A pentose active in biological systems usually in its D-form. D-Ribose,D Ribose

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