(3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester
CAS No.:366785-49-1
Molecular Formula:C₄₂H₅₂N₄O₁₀
Molecular Weight:772.896
Hs Code.:

(3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester

Synonyms:(3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester

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Chemical Property of (3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester

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Technology Process of (3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester

There total 10 articles about (3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl 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:

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

: 366785-49-1
(3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 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

6.1: H₂ / Pd/C / methanol

7.1: 0.088 g / Et₃N; PyBOP / acetonitrile / 7 h

8.1: LiOH; H₂O / tetrahydrofuran / -10 - 20 °C

9.1: 0.066 g / Et₃N; PyBOP / acetonitrile / 3 h

With ruthenium trichloride; lithium hydroxide; sodium hydroxide; sodium periodate; Chirazyme L-2; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; hydrogen; triethylamine; sodium phosphate; palladium on activated charcoal; In tetrahydrofuran; 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

: 366785-49-1
(3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 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

6.1: H₂ / Pd/C / methanol

7.1: 0.088 g / Et₃N; PyBOP / acetonitrile / 7 h

8.1: LiOH; H₂O / tetrahydrofuran / -10 - 20 °C

9.1: 0.066 g / Et₃N; PyBOP / acetonitrile / 3 h

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

Reference yield:

: t-butyl (+/-)-(1S,4R)-2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

: 366785-49-1
(3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

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

2.1: 9.87 g / diethyl ether / 1 h

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

3.2: HCl (g) / ethyl acetate / 0 °C

3.3: HATU; Et₃N / acetonitrile / 18 h

4.1: 89 percent / Et₃N; PyBOP / acetonitrile / 10 h

5.1: H₂ / Pd/C / methanol

6.1: 0.088 g / Et₃N; PyBOP / acetonitrile / 7 h

7.1: LiOH; H₂O / tetrahydrofuran / -10 - 20 °C

8.1: 0.066 g / Et₃N; PyBOP / acetonitrile / 3 h

With ruthenium trichloride; lithium hydroxide; sodium hydroxide; sodium periodate; Chirazyme L-2; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; hydrogen; triethylamine; sodium phosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; ethyl acetate; toluene; acetonitrile;
DOI:10.1021/jo010284l