(2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanoic acid

Base Information

Chemical Name:(2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanoic acid
CAS No.:139374-07-5
Molecular Formula:C₁₇H₂₄N₂O₆
Molecular Weight:352.387
Hs Code.:

Synonyms:(2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanoic acid

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Chemical Property of (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanoic acid

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Technology Process of (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanoic acid

There total 25 articles about (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanoic acid 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: 87.0%

: 370865-56-8
S-(4'-tolyl) (2S,3S)-3-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanethioate

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

Guidance literature:: With sodium hydroxide; dihydrogen peroxide; for 1h;
DOI:10.1055/s-2002-34851

Reference yield: 81.0%

: 139374-06-4
(2R,3S)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-butanol

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

Guidance literature:: With jones reagent; In acetone; at 0 ℃; for 1h;
DOI:10.1246/bcsj.68.1369

Reference yield:

: 2592-18-9
Boc-Thr-OH

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

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide, 2.) NaBH₄ / 1.) THF, a) 0 deg C, 1 h, b) RT, 5 h, 2.) THF, EtOH, 0 deg C, 30 min

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

3: 88 percent / Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

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

5: EtOH / 10percent Pd/C / 2 h / Ambient temperature

6: Et₃N / ethanol / 1 h / Ambient temperature

7: 90 percent / 70percent AcOH / 12 h / Ambient temperature

8: 81 percent / Jones reagent / acetone / 1 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; sodium azide; jones reagent; 15-crown-5; ethanol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; dichloromethane; acetone;
DOI:10.1246/bcsj.68.1369