methyl 2-(2,2,2-trifluoro-acetylamino)-3-carbobenzyloxy-(2S,3S)-hex-5-enoate

Base Information

• Chemical Name: methyl 2-(2,2,2-trifluoro-acetylamino)-3-carbobenzyloxy-(2S,3S)-hex-5-enoate
• CAS No.: 700816-05-3
• Molecular Formula: C₁₇H₁₈F₃NO₅
• Molecular Weight: 373.329

Synonyms:methyl 2-(2,2,2-trifluoro-acetylamino)-3-carbobenzyloxy-(2S,3S)-hex-5-enoate

Chemical Property of methyl 2-(2,2,2-trifluoro-acetylamino)-3-carbobenzyloxy-(2S,3S)-hex-5-enoate

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Technology Process of methyl 2-(2,2,2-trifluoro-acetylamino)-3-carbobenzyloxy-(2S,3S)-hex-5-enoate

There total 2 articles about methyl 2-(2,2,2-trifluoro-acetylamino)-3-carbobenzyloxy-(2S,3S)-hex-5-enoate 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: 72.0%

1-(trifluoroacetyl)benzotriazole (183266-61-7) + methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-(2S,3S)-hex-5-enoate (700816-00-8) → methyl 2-(2,2,2-trifluoro-acetylamino)-3-carbobenzyloxy-(2S,3S)-hex-5-enoate (700816-05-3)

Guidance literature:

methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-(2S,3S)-hex-5-enoate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

1-(trifluoroacetyl)benzotriazole; With TEA; In tetrahydrofuran; dichloromethane; Further stages.;

DOI:10.1016/j.tetlet.2004.02.117

Reference yield:

4-benzyl 1-methyl N-(tert-butoxycarbonyl)-L-aspartate (80963-12-8) → methyl 2-(2,2,2-trifluoro-acetylamino)-3-carbobenzyloxy-(2S,3S)-hex-5-enoate (700816-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium bis(trimethylsilyl)amide; hexamethylphosphoramide / tetrahydrofuran / 0.5 h / -42 °C

1.2: 0.4 g / tetrahydrofuran / 4 h / -42 °C

2.1: aq. trifluoroacetic acid / CH₂Cl₂ / 0 - 20 °C

2.2: 72 percent / TEA / tetrahydrofuran; CH₂Cl₂

With N,N,N,N,N,N-hexamethylphosphoric triamide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2004.02.117

Reference yield:

methyl 2-(2,2,2-trifluoro-acetylamino)-3-carbobenzyloxy-(2S,3S)-hex-5-enoate (700816-05-3) → (2S,3S)-2-(2-Oxo-ethyl)-3-(2,2,2-trifluoro-acetylamino)-succinic acid 1-benzyl ester 4-methyl ester (700816-06-4)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; water;

DOI:10.1016/j.tetlet.2004.02.117

upstream raw materials:

1-(trifluoroacetyl)benzotriazole

methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-(2S,3S)-hex-5-enoate

4-benzyl 1-methyl N-(tert-butoxycarbonyl)-L-aspartate

Downstream raw materials:

(2S,3S)-2-(2-Oxo-ethyl)-3-(2,2,2-trifluoro-acetylamino)-succinic acid 1-benzyl ester 4-methyl ester

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