Asymmetric Hydrolysis of Prochiral Diesters with Pig Liver Esterase. Preparation of Optically Active Intermediates for the Synthesis of ( + )-Biotin and (+)-α-Methyl-3, 4-dihydroxyphenylalanine
スポンサーリンク
概要
- 論文の詳細を見る
With pig liver esterase, 1, 3-dibenzyl-4, 5-cis-bis(alkyloxycarbonyl)-2-oxoimidazolidine (1) was asymmetrically hydrolyzed to (4S, 5R)-l, 3-dibenzyl-5-alkyloxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (2). This acid 2 was reduced with lithium borohydride to (4S, 5R)-l, 3-dibenzyl-5-hydroxymethyl-2-oxoimidazolidine-4-carboxylic acid lactone (3), which is known to be converted to ( + )-biotin (4). With the same esterase, diethyl 3, 4-dimethoxyphenylmethyl-(methyl)malonate (5) was asymmetrically hydrolyzed to (R)-ethyl hydrogen 3, 4-dimethoxy-phenylmethyl(methyl)malonate (6), which can be converted to (S)-α-methyl-3, 4-dihydroxyphenyl-alanine(L-a-methyldopa) (9).
- 社団法人 日本農芸化学会の論文
著者
-
HASEGAWA Keiko
Sagami Chemical Research Center
-
IRIUCHIJIMA Shinobu
Sagami Chemical Research Center
-
TSUCHIHASHI Gen-ichi
Sagami Chemical Research Center
関連論文
- A Convenient Synthesis of Methyl Methylthiomethyl Sulfoxide
- Oxidation of methyl (methylthio)methyl sulfoxide.
- Asymmetric Hydrolysis of Prochiral Diesters with Pig Liver Esterase. Preparation of Optically Active Intermediates for the Synthesis of ( + )-Biotin and (+)-α-Methyl-3, 4-dihydroxyphenylalanine
- Asymmetric Hydrolysis of (±)-1-Acetoxy-2, 3-dichloropropane with Enzymes and Microorganisms
- Stereochemical Studies on the Halogenation of Sulfoxides. II. The Bromination of Cyclic Sulfoxides
- Thiocarbonyl Compounds as Potential Scavengers of Carbon Radicals
- Asymmetric Hydrolysis of (±)-1, 2-Diacetoxy-3-chloropropane and Its Related Compounds with Lipase. Synthesis of Optically Pure (S)-Propranolol
- Stereospecific reductive desulfinylation of 1-aryl-2-(methylsulfinyl)-2-(methylthio)ethenes with Grignard reagents.
- Synthesis of (S,S)-2-amino-3-phenylbutyric acid.
- The α-Chlorination of Sulfoxides with N-Chlorosuccinimide
- Reaction of α-Chloro Sulfoxides with Carbonyl and Thiocarbonyl Compounds
- Rearrangement of Aryl Sulfides in the Presence of Aluminum Chloride