Method of preparing (S)-.gamma.-hydroxymethyl-.alpha., .beta.-bu

Details Method of preparing (S)-.gamma.-hydroxymethyl-.alpha., .beta.-bu Method of preparing (S)-.gamma.-hydroxymethyl-.alpha., .beta.-bu

1990-07-10

1991-02-19

Hollrah, Glennon H.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549397, C07D30728, C07D31100

Patent

active

049945858

ABSTRACT:
A method of preparing (S)-.gamma.-hydroxymethyl-.alpha.,.beta.-butenolide includes the step of oxidizing a levoglucosenone with a peracid in an organic solvent. Peracetic acid, metha-chloroperbenzoic acid or magnesium monoperoxyphthalate hexahydrate can be used as the peracid. According to this method, an (S)-.gamma.-hydroxymethyl-.alpha.,.beta.-butenolide having high optical purity can be easily prepared from a levoglucosenone as a starting material at a high yield.

REFERENCES:
Tetrahedron Letters, vol. 38, No. 15, pp. 2395-2401, P. Camps et al.
Tetrahedron Letters, vol. 30, pp. 3547-3552, M. Taniguchi et al.
Carbohydrate Research, 58 (1977) 79-87, F. Shafizadeh et al.
Tetrahedron Letters, vol. 28, No. 20, pp. 2299-2300, J. A. J. M. Vekemans et al.
Synthesis, pp. 834-835 (1984).
Carbohydrate Research, 71 (1979), pp. 169-191, F. Shafizadeh et al.

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