(2S,3S)-2-[(S)-3-[Benzyloxy-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethoxy)-phosphoryloxy]-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-3-methyl-pentanoic acid benzyl ester

Base Information

• Chemical Name: (2S,3S)-2-[(S)-3-[Benzyloxy-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethoxy)-phosphoryloxy]-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-3-methyl-pentanoic acid benzyl ester
• CAS No.: 146900-37-0
• Molecular Formula: C₅₅H₆₅N₄O₁₄P
• Molecular Weight: 1037.11

Synonyms:

Chemical Property of (2S,3S)-2-[(S)-3-[Benzyloxy-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethoxy)-phosphoryloxy]-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-3-methyl-pentanoic acid benzyl ester

Chemical Property:

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Safty Information:

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MSDS Files:

Useful:

Technology Process of (2S,3S)-2-[(S)-3-[Benzyloxy-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethoxy)-phosphoryloxy]-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-3-methyl-pentanoic acid benzyl ester

There total 4 articles about (2S,3S)-2-[(S)-3-[Benzyloxy-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethoxy)-phosphoryloxy]-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-3-methyl-pentanoic acid benzyl 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:

N-benzyloxycarbonyl-L-threonine benzyl ester (84500-41-4,85995-50-2,85995-51-3,126401-06-7,16597-50-5) → (2S,3S)-2-[(S)-3-[Benzyloxy-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethoxy)-phosphoryloxy]-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-3-methyl-pentanoic acid benzyl ester (146900-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / 1H-tetrazole / CH₂Cl₂; acetonitrile / 0.25 h / 20 °C

2: 1) 1H-tetrazole, 2) t-BuOOH / 1) CH₂Cl₂, CH₃CN, 20 deg C, 25 min, 2) 20 deg C, 15 min

With 1H-tetrazole; tert.-butylhydroperoxide; In dichloromethane; acetonitrile;

DOI:10.1055/s-1992-26355

Reference yield:

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite (108549-21-9) → (2S,3S)-2-[(S)-3-[Benzyloxy-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethoxy)-phosphoryloxy]-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-3-methyl-pentanoic acid benzyl ester (146900-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / 1H-tetrazole / CH₂Cl₂; acetonitrile / 0.25 h / 20 °C

2: 1) 1H-tetrazole, 2) t-BuOOH / 1) CH₂Cl₂, CH₃CN, 20 deg C, 25 min, 2) 20 deg C, 15 min

With 1H-tetrazole; tert.-butylhydroperoxide; In dichloromethane; acetonitrile;

DOI:10.1055/s-1992-26355

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (2S,3S)-2-[(S)-3-[Benzyloxy-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethoxy)-phosphoryloxy]-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-3-methyl-pentanoic acid benzyl ester (146900-37-0)

Guidance literature:

Multi-step reaction with 3 steps

1: NEt₃ / diethyl ether / 1 h / 20 °C

2: 91 percent / 1H-tetrazole / CH₂Cl₂; acetonitrile / 0.25 h / 20 °C

3: 1) 1H-tetrazole, 2) t-BuOOH / 1) CH₂Cl₂, CH₃CN, 20 deg C, 25 min, 2) 20 deg C, 15 min

With 1H-tetrazole; tert.-butylhydroperoxide; triethylamine; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1055/s-1992-26355

upstream raw materials:

(2S,3R)-2-Benzyloxycarbonylamino-3-(benzyloxy-diisopropylamino-phosphanyloxy)-butyric acid benzyl ester

N_α-(benzyloxycarbonyl)valylserylisoleucyl C_α-1-benzyl ester

N-benzyloxycarbonyl-L-threonine benzyl ester

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite

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