methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoate

Base Information

• Chemical Name: methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoate
• CAS No.: 443921-80-0
• Molecular Formula: C₄₂H₄₃N₃O₉
• Molecular Weight: 733.818

Synonyms:methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoate

Chemical Property of methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoate

There total 13 articles about methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoate 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: 67.0%

2-benzyloxycarbonylamino-3-iodo-propionic acid tert-butyl ester (190579-73-8) + methyl (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-(4-iodo-1,3-benzoxazol-2-yl)butanoate (443921-82-2) → methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoate (443921-80-0) + 2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{2'-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methoxycarbonyl-propyl]-[4,4']bibenzooxazolyl-2-yl}-butyric acid methyl ester

Guidance literature:

2-benzyloxycarbonylamino-3-iodo-propionic acid tert-butyl ester; With chloro-trimethyl-silane; zinc; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

methyl (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-(4-iodo-1,3-benzoxazol-2-yl)butanoate; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 25 - 50 ℃; for 2.25h; Further stages.;

DOI:10.1021/jo025615o

Reference yield:

L-glutamic acid 1-methyl ester (6384-08-3) → methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoate (443921-80-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / NaHCO₃ / H₂O; tetrahydrofuran / 16 h / 20 °C

2.1: Et₃N; isobutyl chloroformate / CH₂Cl₂ / 0.5 h / -10 °C

2.2: CH₂Cl₂ / 16 h / -10 - 20 °C

2.3: 68 percent / propionic acid / 3 h / Heating

3.1: Me₃SiCl; Zn / dimethylformamide / 1 h / 20 °C

3.2: 67 percent / PdCl₂(PPh₃)2 / dimethylformamide / 2.25 h / 25 - 50 °C

With chloro-trimethyl-silane; sodium hydrogencarbonate; triethylamine; zinc; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo025615o

Reference yield:

2-amino-3-hydroxy-1-iodobenzene (443921-86-6) → methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoate (443921-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N; isobutyl chloroformate / CH₂Cl₂ / 0.5 h / -10 °C

1.2: CH₂Cl₂ / 16 h / -10 - 20 °C

1.3: 68 percent / propionic acid / 3 h / Heating

2.1: Me₃SiCl; Zn / dimethylformamide / 1 h / 20 °C

2.2: 67 percent / PdCl₂(PPh₃)2 / dimethylformamide / 2.25 h / 25 - 50 °C

With chloro-trimethyl-silane; triethylamine; zinc; isobutyl chloroformate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo025615o

upstream raw materials:

2-benzyloxycarbonylamino-3-iodo-propionic acid tert-butyl ester

methyl (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-(4-iodo-1,3-benzoxazol-2-yl)butanoate

L-glutamic acid 1-methyl ester

2-amino-3-hydroxy-1-iodobenzene

Downstream raw materials:

methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-6-phthalimidohexanoyl]amino}butanoate

methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(benzyloxycarbonyl)propanoyl]amino}butanoate

methyl (7S,10S,13S)-10-(4-phthalimidobutyl)-7-{[(benzyloxy)carbonyl]amino}-8,11-dioxo-19-oxa-9,12,17-triazatricyclo[14.2.1.0^6,18]nonadeca-1⁽¹⁸⁾,2,4,16-tetraene-13-carboxylate

methyl (2S)-4-{4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(tert-butoxy)-3-oxopropyl]-1,3-benzoxazol-2-yl}-2-{[(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl]amino}butanoate

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