(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester

Base Information

• Chemical Name: (2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester
• CAS No.: 397883-86-2
• Molecular Formula: C₆₂H₆₉N₄O₁₄P
• Molecular Weight: 1125.22

Synonyms:(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester

Chemical Property of (2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester

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Technology Process of (2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester

There total 2 articles about (2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-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-acetyl-L-tyrosine (537-55-3) → (2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester (397883-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydroxybenzotriazole; dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 0 °C

1.2: NMM / tetrahydrofuran / 0 - 20 °C

2.1: 1-H-tetrazole / tetrahydrofuran / 20 °C

2.2: 93 percent / aq. tert-butyl hydroperoxide / tetrahydrofuran / -10 - 20 °C

With 1H-tetrazole; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1021/ja011746f

Reference yield:

(2S,3S)-2-[(S)-2-((S)-2-Amino-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester; hydrochloride → (2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester (397883-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydroxybenzotriazole; dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 0 °C

1.2: NMM / tetrahydrofuran / 0 - 20 °C

2.1: 1-H-tetrazole / tetrahydrofuran / 20 °C

2.2: 93 percent / aq. tert-butyl hydroperoxide / tetrahydrofuran / -10 - 20 °C

With 1H-tetrazole; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1021/ja011746f

Reference yield: 100.0%

(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester (397883-86-2) → Ac-pTyr-Glu-Glu-Ile-OH

Guidance literature:

(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-benzyloxycarbonyl-butyrylamino)-4-benzyloxycarbonyl-butyrylamino]-3-methyl-pentanoic acid benzyl ester; palladium on activated charcoal; In ethanol; for 0.5h; under 760.051 Torr;

With water; Further stages.;

DOI:10.1021/ja011746f

upstream raw materials:

N-acetyl-L-tyrosine

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