Method of producing (S)-4-hydroxymethyl-.gamma.-lactone

Details Method of producing (S)-4-hydroxymethyl-.gamma.-lactone Method of producing (S)-4-hydroxymethyl-.gamma.-lactone

1990-09-17

1992-05-12

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30778

Patent

active

051129949

ABSTRACT:
(S)-4-hydroxymethyl-.gamma.-lactone is prepared by oxidizing dihydrolevoglucosenone with a peracid in an organic solvent. (S)-4-hydroxymethyl-.gamma.-lactone is prepared from levoglucosenone. First, levoglucosenone is catalytic hydrogenated, thereby dihydrolevoglucosenone is obtained. Next, dihydrolevoglucosenone thus obtained is oxidized with a peracid in an organic solvent, thereby (S)-4-hydroxymethyl-.gamma.-lactone is obtained. In this manner, (S)-4-hydroxymethyl-.gamma.-lactone can be obtained with high optical purity.

REFERENCES:
patent: 3926947 (1975-12-01), Lipska
patent: 4673759 (1987-06-01), Dalcanale
patent: 4959161 (1990-09-01), Clubley
patent: 4994585 (1991-02-01), Koseki et al.
Tetrahedron, "Stereoselective Synthesis of D-Ribose from L-Glutamic Acid", vol. 30, No. 19, 1974, pp. 3547-3552, M. Taniguchi et al.
Journal of Organic Chemistry, "Synthesis of the Dideoxynucleosides ddC and CNT from Glutamic Acid, . . . ", vol. 53, 1988, pp. 4780-4789, Masami Okabe et al.
Heterocycles, "A Method for Easy Preparation of Optically Pure (S)-5-Hydroxy-2-Penten-4-Olide and (S)-5-Hydroxy . . . ", vol. 30, No. 3, 1990, pp. 423-426, Koshi Koseki et al.
Lipska et al., J. of App. Polymer Sci., vol. 15, pp. 419-435 (1971).
Halpern et al., J. Org. Chem., vol. 28, No. 2, pp. 204-209 (1973).

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