(3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

Base Information

Chemical Name:(3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester
CAS No.:366785-47-9
Molecular Formula:C₂₇H₃₂N₂O₈
Molecular Weight:512.56
Hs Code.:

Synonyms:(3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

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Chemical Property of (3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

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Technology Process of (3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

There total 6 articles about (3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

: 962-39-0
L-Phenylalanine benzyl ester

: 366785-43-5
(3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester

: 366785-47-9
(3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

Guidance literature:: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In acetonitrile; for 10h;
DOI:10.1021/jo010284l

Reference yield:

: 36016-38-3
tert-Butyl N-hydroxycarbamate

: 366785-47-9
(3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 74 percent / NaIO₄ / methanol; H₂O / 0.5 h / 0 °C

2.1: NaIO₄; RuCl₃*H₂O / ethyl acetate; acetonitrile; H₂O / 2 h / 20 °C

3.1: 9.87 g / diethyl ether / 1 h

4.1: Chirazyme L-2; sodium phosphate; NaOH / toluene; H₂O / 8 h / pH 7.6 - 7.8

4.2: HCl (g) / ethyl acetate / 0 °C

4.3: HATU; Et₃N / acetonitrile / 18 h

5.1: 89 percent / Et₃N; PyBOP / acetonitrile / 10 h

With ruthenium trichloride; sodium hydroxide; sodium periodate; Chirazyme L-2; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; sodium phosphate; In methanol; diethyl ether; water; ethyl acetate; toluene; acetonitrile; 1.1: Diels-Alder reaction;
DOI:10.1021/jo010284l

Reference yield:

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 366785-47-9
(3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 74 percent / NaIO₄ / methanol; H₂O / 0.5 h / 0 °C

2.1: NaIO₄; RuCl₃*H₂O / ethyl acetate; acetonitrile; H₂O / 2 h / 20 °C

3.1: 9.87 g / diethyl ether / 1 h

4.1: Chirazyme L-2; sodium phosphate; NaOH / toluene; H₂O / 8 h / pH 7.6 - 7.8

4.2: HCl (g) / ethyl acetate / 0 °C

4.3: HATU; Et₃N / acetonitrile / 18 h

5.1: 89 percent / Et₃N; PyBOP / acetonitrile / 10 h

With ruthenium trichloride; sodium hydroxide; sodium periodate; Chirazyme L-2; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; sodium phosphate; In methanol; diethyl ether; water; ethyl acetate; toluene; acetonitrile; 1.1: Diels-Alder reaction;
DOI:10.1021/jo010284l