(S)-1-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester

Base Information

• Chemical Name: (S)-1-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester
• CAS No.: 462117-74-4
• Molecular Formula: C₄₃H₅₅N₃O₁₀
• Molecular Weight: 773.924
• Mol file: 462117-74-4.mol

Synonyms:

Chemical Property of (S)-1-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester

There total 5 articles about (S)-1-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl 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:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → (S)-1-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester (462117-74-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / DCC; DMAP

2: 100 percent / TFA

3: 55 percent / BOP-Cl

With dmap; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; dicyclohexyl-carbodiimide; trifluoroacetic acid;

DOI:10.1016/S0960-894X(02)00214-7

Reference yield:

O-benzyl-L-threonine (4378-10-3) → (S)-1-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester (462117-74-4)

Guidance literature:

Multi-step reaction with 5 steps

1: NaNO₂; H₂SO₄

2: Cs₂CO₃

3: 77 percent / DCC; DMAP

4: 100 percent / TFA

5: 55 percent / BOP-Cl

With dmap; sulfuric acid; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; caesium carbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium nitrite;

DOI:10.1016/S0960-894X(02)00214-7

Reference yield:

(2S,3R)-3-(benzyloxy)-2-hydroxybutanoic acid (669738-91-4) → (S)-1-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester (462117-74-4)

Guidance literature:

Multi-step reaction with 4 steps

1: Cs₂CO₃

2: 77 percent / DCC; DMAP

3: 100 percent / TFA

4: 55 percent / BOP-Cl

With dmap; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; caesium carbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid;

DOI:10.1016/S0960-894X(02)00214-7

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

O-benzyl-L-threonine

(2S,3R)-3-(benzyloxy)-2-hydroxybutanoic acid

(2S,3R)-3-Benzyloxy-2-hydroxy-butyric acid benzyl ester

Downstream raw materials:

(S)-1-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester

C₄₅H₇₁N₇O₁₅

C₅₉H₈₃N₇O₁₅