反応 #2348111

ord-1371dba79beb42a09dabbd1cb50a9952

反応方程式

CCCCCC
hexane
CC(=O)OC1=CC(C)CCCCCCCCCCCC1
3-methylcyclopentadecene-1-yl acetate
CCCCCC
hexane
CC1CCCCCCCCCCCCC(=O)C1
3-methylcyclopentadecanone
CC(=O)OC1=CC(C)CCCCCCCCCCCC1
3-methylcyclopentadecene-1-yl acetate

溶媒

反応条件

温度
55°CELSIUS
詳細条件
See reaction.notes.procedure_details.

実験手順

Mixed in 20 mL of a phosphate buffer (pH 7) were 2.0 g of dl-3-methylcyclopentadecene-1-yl acetate as obtained in Example 1 (a) and 1.0 g (50 wt. % relative to the substrate) of the immobilized enzyme (Novozyme 435) originating from Candida antarctica, followed by vigorous shaking at 55° C. for 2 days. After the reaction, 20 mL of hexane was added to the reaction solution for extraction, and analysis of the hexane layer showed that the conversion of the substrate was 69.8% and that 3-methylcyclopentadecanone was produced, while 3-methylcyclopentadecene-1-yl acetate remained. The hexane solution was purified by silica-gel column chromatography, and 3-methylcyclopentadecanone, as produced by hydrolyzing a portion of the remained 3-methylcyclopentadecene-1-yl acetate by the conventional method, was subjected to determination of the optical purity by HPLC and identified as the (S) isomer with 90.8% ee of optical purity. Also, 3-methylcyclopentadecanone, a enzymatic hydrolysate of the substrate, was subjected to determination of the optical purity and identified as the (R) isomer with 42.6% ee of optical purity.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07846701B2uspto-grants-2010_12