(2S,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid 2,2,2-trichloro-ethyl ester

Base Information

Chemical Name:(2S,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid 2,2,2-trichloro-ethyl ester
CAS No.:139374-11-1
Molecular Formula:C₁₉H₂₅Cl₃N₂O₆
Molecular Weight:483.776
Hs Code.:

Synonyms:(2S,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid 2,2,2-trichloro-ethyl ester

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Chemical Property of (2S,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid 2,2,2-trichloro-ethyl ester

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Technology Process of (2S,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid 2,2,2-trichloro-ethyl ester

There total 8 articles about (2S,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid 2,2,2-trichloro-ethyl 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: 97.0%

: 115-20-8
1,1,1-trichloroethanol

: 139374-07-5
(2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanoic acid

: 139374-11-1
(2S,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid 2,2,2-trichloro-ethyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1246/cl.1992.49

Reference yield:

: 2592-18-9
Boc-Thr-OH

: 139374-11-1
(2S,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid 2,2,2-trichloro-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1) dicyclohexylcarbodiimide 2) NaBH₄ / 1) THF, 0 deg C / 1 h -> r.t. / 5 h 2) 30 min

2: 71 percent / 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 6 h / Ambient temperature

3: 88 percent / Et₃N / CH₂Cl₂ / 30 min / cooling -> r.t. / 4 h

4: 87 percent / NaN₃, 15-crown-5 / hexamethylphosphoric acid triamide / 3 h / 55 °C

5: 1) H₂ 2) Et₃N / 1) Pd/C / 1) EtOH, r.t., 2 h

6: 90 percent / 70percent aq. AcOH

7: 75 percent / Jones reagent / acetone / 1 h / 0 °C

8: 97 percent / DCC, DMAP / CH₂Cl₂

With dmap; sodium tetrahydroborate; sodium azide; jones reagent; 15-crown-5; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetone;
DOI:10.1246/cl.1992.49

Reference yield:

: 99216-67-8,766514-03-8
2-<<(tert-butoxy)carbonyl>amino>butane-1,3-diol

: 139374-11-1
(2S,3S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid 2,2,2-trichloro-ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 71 percent / 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 6 h / Ambient temperature

2: 88 percent / Et₃N / CH₂Cl₂ / 30 min / cooling -> r.t. / 4 h

3: 87 percent / NaN₃, 15-crown-5 / hexamethylphosphoric acid triamide / 3 h / 55 °C

4: 1) H₂ 2) Et₃N / 1) Pd/C / 1) EtOH, r.t., 2 h

5: 90 percent / 70percent aq. AcOH

6: 75 percent / Jones reagent / acetone / 1 h / 0 °C

7: 97 percent / DCC, DMAP / CH₂Cl₂

With dmap; sodium azide; jones reagent; 15-crown-5; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetone;
DOI:10.1246/cl.1992.49