Method for the preparation of 1,4,-anhydro-2-deoxy-d-erythropent

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 111, C07H 100, C07H 1502

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057895724

ABSTRACT:
Proposed is a novel synthetic route for the preparation of 1,4-anhydro-2-deoxy-D-erythropentitol, which is a useful material in the synthesis of antibiotics, starting from 2-deoxy-D-ribose via 2-deoxy-D-erythropentitol as an intermediate. 2-Deoxy-D-erythropentitol can be prepared by the hydrogenation of 2-deoxy-D-ribose with Raney nickel as the hydrogenating catalyst in a high efficiency and at low costs as compared with the prior art methods using, for example, sodium borohydride as the hydrogenating agent. 2-Deoxy-D-erythropentitol is subjected to a dehydration cyclization reaction to be converted into 1,4-anhydro-2-deoxy-D-erythropenti-tol under a substantially anhydrous condition which is accomplished by heating a reaction mixture containing 2-deoxy-D-erythropentitol suspended in an organic solvent capable of forming an azeotropic mixture with water such as toluene under reflux so as to azeotropically remove the water condensate.

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