2-{(R)-2-benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(1-carboxyethylcarbamoyl)ethyldisulfanyl]propionylamino}propionic acid

Base Information

• Chemical Name: 2-{(R)-2-benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(1-carboxyethylcarbamoyl)ethyldisulfanyl]propionylamino}propionic acid
• CAS No.: 339205-35-5
• Molecular Formula: C₂₈H₃₄N₄O₁₀S₂
• Molecular Weight: 650.731

Synonyms:2-{(R)-2-benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(1-carboxyethylcarbamoyl)ethyldisulfanyl]propionylamino}propionic acid

Chemical Property of 2-{(R)-2-benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(1-carboxyethylcarbamoyl)ethyldisulfanyl]propionylamino}propionic acid

Chemical Property:

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Technology Process of 2-{(R)-2-benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(1-carboxyethylcarbamoyl)ethyldisulfanyl]propionylamino}propionic acid

There total 5 articles about 2-{(R)-2-benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(1-carboxyethylcarbamoyl)ethyldisulfanyl]propionylamino}propionic acid 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: 91.0%

benzyl N-[(1R)-1-({[(2R)-2-(benzylcarbonyl)amino-3-(1H-1,2,3-benzotriazol-1-yl)-3-oxopropyl]disulfanyl}methyl)-2-(1H-1,2,3-benzotriazol-1-yl)-2-oxoethyl]carbamate (886981-18-6) + rac-Ala-OH (302-72-7,25191-17-7,18875-37-1) → 2-{(R)-2-benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(1-carboxyethylcarbamoyl)ethyldisulfanyl]propionylamino}propionic acid (339205-35-5)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1055/s-2006-926287

Reference yield: 70.0%

(Z-L-Cys-DL-AlaOMe)2 (339175-15-4) → 2-{(R)-2-benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(1-carboxyethylcarbamoyl)ethyldisulfanyl]propionylamino}propionic acid (339205-35-5)

Guidance literature:

With lithium hydroxide; In methanol; at 5 ℃; for 18h;

DOI:10.1016/S0968-0896(00)00257-1

Reference yield:

L-cystine (56-89-3) → 2-{(R)-2-benzyloxycarbonylamino-3-[(R)-2-benzyloxycarbonylamino-2-(1-carboxyethylcarbamoyl)ethyldisulfanyl]propionylamino}propionic acid (339205-35-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / dicyclohexylcarbodiimide; Et₃N / CH₂Cl₂ / 0 - 20 °C

2: 70 percent / aq. LiOH / methanol / 18 h / 5 °C

With lithium hydroxide; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 1: condensation / 2: condensation / 3: hydrolysis;

DOI:10.1016/S0968-0896(00)00257-1

upstream raw materials:

(Z-L-Cys-DL-AlaOMe)2

benzyl N-[(1R)-1-({[(2R)-2-(benzylcarbonyl)amino-3-(1H-1,2,3-benzotriazol-1-yl)-3-oxopropyl]disulfanyl}methyl)-2-(1H-1,2,3-benzotriazol-1-yl)-2-oxoethyl]carbamate

rac-Ala-OH

L-cystine

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