(E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester

Base Information

• Chemical Name: (E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester
• CAS No.: 446064-64-8
• Molecular Formula: C₂₈H₄₅NO₅Si
• Molecular Weight: 503.755

Synonyms:(E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester

Chemical Property of (E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester

Chemical Property:

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Technology Process of (E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester

There total 2 articles about (E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl 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: 95.0%

allyl (triphenylphosphoranylidene)acetate (104127-76-6) + [(S)-1-Formyl-2-(4-triisopropylsilanyloxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (151133-13-0) → (E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester (446064-64-8)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1016/S0040-4020(02)00627-0

Reference yield:

(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(triisopropylsilyloxy)phenyl)propanoate (735327-63-6) → (E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester (446064-64-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / DIBAL-H

2: 95 percent / dimethylformamide / 5 h / 20 °C

With diisobutylaluminium hydride; In N,N-dimethyl-formamide; 2: Wittig reaction;

DOI:10.1016/S0040-4020(02)00627-0

Reference yield:

(E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester (446064-64-8) → (E)-(S)-4-Amino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester

Guidance literature:

With trifluoroacetic acid;

DOI:10.1016/S0040-4039(02)00599-3

upstream raw materials:

allyl (triphenylphosphoranylidene)acetate

[(S)-1-Formyl-2-(4-triisopropylsilanyloxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(triisopropylsilyloxy)phenyl)propanoate

Downstream raw materials:

(E)-(S)-4-((2R,3S)-2-Amino-3-methyl-pentanoylamino)-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester

(E)-(S)-4-((2R,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid allyl ester

C₆₅H₉₀Cl₃N₉O₁₆Si

C₆₈H₉₄Cl₃N₉O₁₆Si

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