(S)-2-[(S)-3-(5-Benzyloxy-2-nitro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(S)-3-(5-Benzyloxy-2-nitro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid methyl ester
• CAS No.: 1027080-01-8
• Molecular Formula: C₃₅H₃₃N₃O₈
• Molecular Weight: 623.662
• Mol file: 1027080-01-8.mol

Synonyms:

Chemical Property of (S)-2-[(S)-3-(5-Benzyloxy-2-nitro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(S)-3-(5-Benzyloxy-2-nitro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid methyl ester

There total 10 articles about (S)-2-[(S)-3-(5-Benzyloxy-2-nitro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic 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:

(5-(benzyloxy)-2-nitrophenyl)methanol (68423-36-9) → (S)-2-[(S)-3-(5-Benzyloxy-2-nitro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid methyl ester (1027080-01-8)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N / tetrahydrofuran / 1 h / 0 °C

2: NaI / acetone / 2 h / Ambient temperature

3: 78 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 15 min, 2.) r.t., overnight

4: aq. LiOH, LiBr, tetrabutylammonium bromide / acetonitrile / 3 h / Ambient temperature

5: Et₃N / methanol / 8 h / Ambient temperature

6: DCC / CH₂Cl₂

7: Et₃N / dimethylformamide

With lithium hydroxide; n-butyllithium; tetrabutylammomium bromide; triethylamine; dicyclohexyl-carbodiimide; sodium iodide; lithium bromide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo00108a023

Reference yield:

3-hydroxymethyl-4-nitrophenol (60463-12-9) → (S)-2-[(S)-3-(5-Benzyloxy-2-nitro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid methyl ester (1027080-01-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / NaH / tetrahydrofuran; dimethylformamide / 1.) 30-40 deg C, 30 min, 2.) r.t., 2 h

2: Et₃N / tetrahydrofuran / 1 h / 0 °C

3: NaI / acetone / 2 h / Ambient temperature

4: 78 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 15 min, 2.) r.t., overnight

5: aq. LiOH, LiBr, tetrabutylammonium bromide / acetonitrile / 3 h / Ambient temperature

6: Et₃N / methanol / 8 h / Ambient temperature

7: DCC / CH₂Cl₂

8: Et₃N / dimethylformamide

With lithium hydroxide; n-butyllithium; tetrabutylammomium bromide; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; sodium iodide; lithium bromide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo00108a023

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-2-[(S)-3-(5-Benzyloxy-2-nitro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid methyl ester (1027080-01-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / methanol / 8 h / Ambient temperature

2: DCC / CH₂Cl₂

3: Et₃N / dimethylformamide

With triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00108a023

upstream raw materials:

L-alanine methyl ester hydrochloride

(5-(benzyloxy)-2-nitrophenyl)methanol

3-hydroxymethyl-4-nitrophenol

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Downstream raw materials:

(S)-2-[(S)-2-Acetylamino-3-(2-amino-5-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester

Ac-L-m-Nip(Bn)-Ala-OMe

(S)-2-[(S)-2-Amino-3-(5-benzyloxy-2-nitro-phenyl)-propionylamino]-propionic acid methyl ester