(S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate

Base Information

• Chemical Name: (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate
• CAS No.: 503416-72-6
• Molecular Formula: C₃₀H₃₅NO₆
• Molecular Weight: 505.611

Synonyms:(S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate

Chemical Property of (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate

Chemical Property:

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Technology Process of (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate

There total 9 articles about (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate 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: 63.0%

methanol (67-56-1) + Boc-(L)-DOPA[OBn]2-CHN2 (503416-71-5) → (S)-methyl N-(tert-butyloxycarbonyl)-β3-homo-3,4-bis(benzyloxy)phenylalanine carboxylate (503416-72-6)

Guidance literature:

With silver benzoate; triethylamine; at -25 - 20 ℃;

DOI:10.1016/S0040-4039(02)02035-X

Reference yield:

methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate (37169-36-1) → (S)-methyl N-(tert-butyloxycarbonyl)-β3-homo-3,4-bis(benzyloxy)phenylalanine carboxylate (503416-72-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / potassium carbonate; sodium iodide; n-Bu₄N⁽¹⁺⁾*Br^(1-) / acetone / 4 h / Heating

2: 97 percent / sodium hydroxide / methanol; tetrahydrofuran; H₂O / 24 h / 20 °C

3: triethylamine / tetrahydrofuran / -15 - 0 °C

4: 5.94 g / tetrahydrofuran; diethyl ether / 18 h / 20 °C

5: 61 percent / silver(I) benzoate; triethylamine / tetrahydrofuran / 3 h / 20 °C

With sodium hydroxide; tetrabutylammomium bromide; silver benzoate; potassium carbonate; triethylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; water; acetone; 5: Arndt-Eistert homologation;

DOI:10.1016/j.tetasy.2004.11.089

Reference yield:

3-[3,4-di(benzyloxy)phenyl]-2-{[(tert-butoxy)carbonyl]amino}propanoic acid (59727-98-9) → (S)-methyl N-(tert-butyloxycarbonyl)-β3-homo-3,4-bis(benzyloxy)phenylalanine carboxylate (503416-72-6)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / -15 - 0 °C

2: 5.94 g / tetrahydrofuran; diethyl ether / 18 h / 20 °C

3: 61 percent / silver(I) benzoate; triethylamine / tetrahydrofuran / 3 h / 20 °C

With silver benzoate; triethylamine; In tetrahydrofuran; diethyl ether; 3: Arndt-Eistert homologation;

DOI:10.1016/j.tetasy.2004.11.089

upstream raw materials:

methanol

Boc-(L)-DOPA[OBn]2-CHN₂

di-tert-butyl dicarbonate

levodopa

Downstream raw materials:

(S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(hydroxy)phenylalanine carboxylate

(S)-3-Amino-4-(3,4-bis-benzyloxy-phenyl)-butyric acid methyl ester

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