Enzymatic Preparation of Optically Active Organosilicon Compounds in Organic Solvents

2.2.1. Preparation of Optically Active Trimethylsilylpropanols

1. Trimethylsilylpropanols (donated by Nitto Denko, Osaka, Japan): (R,S)-l-trimethylsilyl-2-propanol (1a), (R,S)-l-trimethylsilyl-l-propanol (2a), and (R,S)-2-trimethylsilyl-l-propanol (3a).

2. Carbon analogs (for comparison): 4,4-dimethyl-2-pentanol (1b) (Aldrich), 2,2-dim-ethyl-3-pentanol (2b) (Aldrich), and 2,3,3-trimethyl-l-butanol (3b) (see Note 13).

3. 5-Phenylpentanoic acid.

4. Water-saturated isooctane.

5. Celite No. 535 (Wako Pure Chemical Industries).

6. Hydrolases: lipase OF 360 from Candida cylindracea (Meito Sangyo), lipase Saiken 100 from Rhizopus japonicus (Osaka Saikin Kenkyusho, Osaka, Japan), lipase (Steapsin) from hog pancreas (Tokyo Kasei, Tokyo, Japan), lipoprotein lipase Type A from Pseudomonas sp. (Toyobo), and cholesterol esterase Type A from Pseudomonas sp. (Toyobo).

7. Sumichiral OA-4600 column (4.0 x 250 mm; Sumika Chemical Analysis Service, Osaka, Japan)

8. 3,5-Dinitro isocyanate (Sumika Chemical Analysis Service).

9. Mobil phase for high-performance liquid chromatography (HPLC): n-hexane/ 2-propanol (100:1 v/v) or n-hexane/2-propanol (98:2 v/v).

11. (R)-Methoxytrifluoromethylphenylacetic acid [(R)-MTPA] (Nacalai Tesque).

2.2.2. Preparation of Optically Active Silylmethanol Derivatives Having a Stereogenic Silicon Atom

1. Racemic alcohols having a stereogenic silicon atom (see Note 14): ethylmethyl-phenylsilylmethanol (see Note 4), 2-(ethylmethylphenylsilyl)ethanol (see Note 5), 3(ethylmethylphenylsilyl)propanol (see Note 6), methylphenyl-n-propylsilylmethanol (see Note 7), n-hexylmethylphenyl-silylmethanol (see Note 8), ethylmethyl (p-methylphenyl)silylmethanol (see Note 9), ethyl(p-fluorophenyl)methyl-silylmethanol (see Note 10), ethyl-n-hexylmethylsilylmethanol (see Note 11), and ethylmethyl-n-propylsilylmethanol (see Note 12).

2. 5-Phenylpentanoic acid.

3. Water-saturated isooctane.

4. Celite No. 535 (Wako Pure Chemical Industries).

5. Papain (crude powder) from Papaya latex (Sigma, St. Louis, MO).

6. Silica gel 60 (Merck)

7. Sumichiral OA-4600 column (4.0 mm x 250 mm, Sumika Chemical Analysis Service).

8. 3,5-Dinitrophenyl isocyanate (Sumika Chemical Analysis Service).

9. Mobil phase for HPLC: n-hexane/2-propanol (98:2 v/v).

10. (S)-Cyanofluorophenylacetic acid [(S)-CFPA] (see Note 15).

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