(2S,3R)-3-Benzyloxy-2-[(S)-2-((S)-2-{2-[(S)-3-benzyloxy-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionylamino]-acetylamino}-3-benzyloxycarbonyl-propionylamino)-4-benzyloxycarbonyl-butyrylamino]-butyric acid methyl ester

Base Information

• Chemical Name: (2S,3R)-3-Benzyloxy-2-[(S)-2-((S)-2-{2-[(S)-3-benzyloxy-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionylamino]-acetylamino}-3-benzyloxycarbonyl-propionylamino)-4-benzyloxycarbonyl-butyrylamino]-butyric acid methyl ester
• CAS No.: 189941-40-0
• Molecular Formula: C₅₈H₆₆N₆O₁₆
• Molecular Weight: 1103.19

Synonyms:

Chemical Property of (2S,3R)-3-Benzyloxy-2-[(S)-2-((S)-2-{2-[(S)-3-benzyloxy-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionylamino]-acetylamino}-3-benzyloxycarbonyl-propionylamino)-4-benzyloxycarbonyl-butyrylamino]-butyric acid methyl ester

Chemical Property:

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Technology Process of (2S,3R)-3-Benzyloxy-2-[(S)-2-((S)-2-{2-[(S)-3-benzyloxy-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionylamino]-acetylamino}-3-benzyloxycarbonyl-propionylamino)-4-benzyloxycarbonyl-butyrylamino]-butyric acid methyl ester

There total 11 articles about (2S,3R)-3-Benzyloxy-2-[(S)-2-((S)-2-{2-[(S)-3-benzyloxy-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionylamino]-acetylamino}-3-benzyloxycarbonyl-propionylamino)-4-benzyloxycarbonyl-butyrylamino]-butyric acid methyl 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: 62.0%

[(S)-3-Benzyloxy-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionylamino]-acetic acid (189941-38-6) + (2S,3R)-2-[(S)-2-((S)-2-Amino-3-benzyloxycarbonyl-propionylamino)-4-benzyloxycarbonyl-butyrylamino]-3-benzyloxy-butyric acid methyl ester (189941-39-7) → (2S,3R)-3-Benzyloxy-2-[(S)-2-((S)-2-{2-[(S)-3-benzyloxy-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionylamino]-acetylamino}-3-benzyloxycarbonyl-propionylamino)-4-benzyloxycarbonyl-butyrylamino]-butyric acid methyl ester (189941-40-0)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1248/cpb.45.643

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → (2S,3R)-3-Benzyloxy-2-[(S)-2-((S)-2-{2-[(S)-3-benzyloxy-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionylamino]-acetylamino}-3-benzyloxycarbonyl-propionylamino)-4-benzyloxycarbonyl-butyrylamino]-butyric acid methyl ester (189941-40-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 34 percent / Et₃N, diethylphosphorocyanidate / CH₂Cl₂; tetrahydrofuran / 4 h / 0 °C

2: 94 percent / NaOMe / methanol; H₂O / 0.5 h / Ambient temperature

3: 62 percent / N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / CH₂Cl₂ / 24 h / Ambient temperature

With diethyl cyanophosphonate; sodium methylate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1248/cpb.45.643

Reference yield:

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → (2S,3R)-3-Benzyloxy-2-[(S)-2-((S)-2-{2-[(S)-3-benzyloxy-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionylamino]-acetylamino}-3-benzyloxycarbonyl-propionylamino)-4-benzyloxycarbonyl-butyrylamino]-butyric acid methyl ester (189941-40-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / Et₃N, diethylphosphorocyanidate / CH₂Cl₂ / 14 h / 0 °C

2: 84 percent / TFA / CH₂Cl₂ / 0.33 h / Ambient temperature

3: 62 percent / N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / CH₂Cl₂ / 24 h / Ambient temperature

With diethyl cyanophosphonate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1248/cpb.45.643

upstream raw materials:

[(S)-3-Benzyloxy-2-((S)-2-benzyloxycarbonylamino-3-hydroxy-propionylamino)-propionylamino]-acetic acid

(2S,3R)-2-[(S)-2-((S)-2-Amino-3-benzyloxycarbonyl-propionylamino)-4-benzyloxycarbonyl-butyrylamino]-3-benzyloxy-butyric acid methyl ester

N-(benzyloxycarbonyl)-L-serine

BOC-L-aspartic acid 4-benzyl ester

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