Method of producing optically active (S)-7-hydroxy-6-methylheptan-2-one and precursor thereof
AssigneeSumitomo Chemical Company, Limited
InventorsNobushige Itaya, Hiroshi Maeda, Yuki Sato
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Abstract
Provided is a method capable of industrially producing optically active (S)-7-hydroxy-6-methylheptan-2-one and its precursor simply and efficiently. The production method, allows a R-body preferentially hydrolyzable Aspergillus microorganism-derived esterase to act on a 2-methyl-6-oxoheptanoate (II), to produce an optically active (S)-2-methyl-6-oxoheptanoate (III).
Claims13
A method of producing an optically active (S)-2-methyl-6-oxoheptanoate, comprising allowing a R-body preferentially hydrolyzable Aspergillus microorganism-derived esterase to act on a 2-methyl-6-oxoheptanoate of the formula (II):
- (wherein, R1 represents an alkyl group having 1 to 5 carbon atoms)
- to cause optical resolution, thereby producing an optically active (S)-2-methyl-6-oxoheptanoate of the formula (III):
- (wherein, R1 represents the same meaning as described above).
A method of producing optically active (S)-7-hydroxy-6-methylheptan-2-one of the formula (I), comprising the steps of
- allowing a R-body preferentially hydrolyzable Aspergillus microorganism-derived esterase to act on a 2-methyl-6-oxoheptanoate of the formula (II):
- (wherein, R1 represents the same meaning as described above)
- to cause optical resolution, thereby producing an optically active (S)-2-methyl-6-oxoheptanoate of the formula (III):
- (wherein, R1 represents the same meaning as described above),
- protecting a carbonyl group of the optically active (S)-2-methyl-6-oxoheptanoate of the formula (III) to obtain an optically active (S)-ketal ester of the formula (IV):
- (wherein, A, R1, R2 and R3 represent the same meanings as described above),
- reducing the optically active (S)-ketal ester of the formula (IV) to obtain an optically active (S)-ketal alcohol of the formula (V):
- (wherein, A, R2 and R3 represent the same meanings as described above), and
- de-protecting the optically active (S)-ketal alcohol of the formula (V) to obtain optically active (S)-7-hydroxy-6-methylheptan-2-one of the formula (I):
Dependencies are inferred from the claim text.