N-tert-Butoxycarbonyl-L-serine

N-tert-Butoxycarbonyl-L-serinal from D-Glucosamine Hydrochloride. T. Henk, T. Kolter, and A. Giannis, Institut fOr Organische Chemie und Biochemie der Universitat Bonn, Gerhaid-Domagk-Str. 1,... 

SYNTHESIS OF N-tert-BUTOXYCARBONYL-L-SERINE p-LACTONE AND THE p-TOLUENESULFONIC ACID SALT OF... 

A- N-(tert-Butoxycarbonyl)-L-serine fi-lactona. A 2-L, three-necked, round-bottomed flask is equipped with a magnetic stirring bar, an argon inlet adaptor, a low temperature thermometer, and a rubber septum (Note 1). The flask is charged with fetrahydrofuran (1.1 L) and triphenylphosphine (42.1 g, 160 mmol) (Note 2). The triphenylphosphine is dissolved with stirring, and the flask is cooled to -78°C with a dry... 

B. (S)-3 Amlno-2-oxetanone p-toluenesulfdnlc acid saltA A 500-mL, singlenecked, round-bottomed flask Is equipped with a magnetic stirring bar and an argon inlet adaptor (Note 1). The flask is charged with a mixture of N-(tert-butoxycarbonyl)-L-serine p-lactone (14.0 g, 74.8 mmol) and anhydrous p-toluenesulfonic acid (13.5 g,... 

The solution of dried N-(tert-butoxycarbonyl)-L-serine was made up separately in ah addition funnel under an atmosphere of argon. This avoids complications that may arise if the funnel is prefitted on the reaction vessel. 

N-tert-Butoxycarbonyl-L-serine lactone Carbamic acid, (2-oxo-3-oxetanyl)-,... 

Since protein and peptide syntheses are rapidly falling into the hands of organic chemists, four procedures to reach building blocks amino acids in the form of its /8-lactone Na-(BENZYLOXY-CARBONYL)-p-(PYRAZOH-YL)-L-ALANINE and the preparation of both /3-lactones, N-tert-BUTOXYCARBONYL-L-SERINE-p-LACTONE and the p-TOLUENESULFONIC ACID SALT OF (S)-3-AMINO-2-OXE-TANONE are described starting from N-tert-BUTOXYCARBONYL-L-SERINE. A useful S or R serine derivative, 1,1-DIMETHYLETHYL (S) or (R)-4-FORMYL-2,2-DIMETHYL-3-OXAZOLIDINECARBOXYLATEis described followed by the improved preparation of N-(BENZYLOXY-CARBONYD-L-VINYLGLYCINE METHYL ESTER, an important intermediate as well as an important substance in biological processes. 

Triphenylphosphine (obtained from Aldrich Chemical Company, Inc.) and N-tert-butoxycarbonyl-L-serine (obtained from U.S. Biochemical Corporation) were dried over P2O5 for 72 hr and 24 hr, respectively. Tetrahydrofuran was distilled from sodium benzophenone ketyl directly into the glassware (under argon) the day before and stored under argon overnight until used. 

N-tert-Butoxycarbonyl-L-serine P-lactone Carbamic acid, (2-oxo-3-oxetanyl)-, 1.1-dimethylethyl ester. (S)- (11) (98541-64-1)... 

N-tert-Butoxycarbonyl-L-serine Serine, N-carboxy-, N-tert-butyl ester, L- (8) L-Serine, N[(1,1-dimethylethoxy)carbonyl]- (9) (3262-72-4) p-Toluenesulfonic acid monohydrate (8) Benzenesulfonic acid, 4-methyl-, monohydrate (9) (6192-52-5)... 

N-(tert-butoxycarbonyl)-L-aspart-1 -oyl-(L-phenylalanyl-L-serine methyl ester)-... 

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