1-{2-[5-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoylamino]-3-tert-butoxy-butyryl}-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 1-{2-[5-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoylamino]-3-tert-butoxy-butyryl}-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester
• CAS No.: 263846-85-1
• Molecular Formula: C₄₉H₆₆N₄O₁₀
• Molecular Weight: 871.084
• Mol file: 263846-85-1.mol

Synonyms:

Chemical Property of 1-{2-[5-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoylamino]-3-tert-butoxy-butyryl}-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{2-[5-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoylamino]-3-tert-butoxy-butyryl}-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester

There total 6 articles about 1-{2-[5-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoylamino]-3-tert-butoxy-butyryl}-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl 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-carboxybenzyl-L-ornithine (3304-51-6,118578-06-6) → 1-{2-[5-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoylamino]-3-tert-butoxy-butyryl}-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester (263846-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. Na₂CO₃ / dioxane / 0 - 25 °C

2: 11 g / EDAC; HOBT / 25 °C

With sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; 1: Acylation / 2: Acylation;

DOI:10.1016/S0968-0896(00)00097-3

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → 1-{2-[5-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoylamino]-3-tert-butoxy-butyryl}-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester (263846-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. Na₂CO₃ / dioxane / 0 - 25 °C

2: 11 g / EDAC; HOBT / 25 °C

With sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; 1: Acylation / 2: Acylation;

DOI:10.1016/S0968-0896(00)00097-3

Reference yield:

Fmoc-Thr(tBu)-OH (71989-35-0,138797-71-4) → 1-{2-[5-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoylamino]-3-tert-butoxy-butyryl}-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester (263846-85-1)

Guidance literature:

Multi-step reaction with 3 steps

1: EDAC; HOBT / CH₂Cl₂ / 0 - 25 °C

2: Et₂NH / dimethylformamide / 4 h / 25 °C

3: 11 g / EDAC; HOBT / 25 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Substitution / 3: Acylation;

DOI:10.1016/S0968-0896(00)00097-3

upstream raw materials:

N^α-fluorenylmethyloxycarbonyl-N^δ-benzyloxycarbonylornithine

N-carboxybenzyl-L-ornithine

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

Fmoc-Thr(tBu)-OH

Downstream raw materials:

C₇₈H₁₀₃N₉O₁₃

C₇₀H₈₈N₈O₁₁

1-(2-{5-{[1-(2-amino-3-tert-butoxy-butyryl)-4-azido-pyrrolidine-2-carbonyl]-amino}-2-[(4''-pentyloxy-[1,1';4',1'']terphenyl-4-carbonyl)-amino]-pentanoylamino}-3-tert-butoxy-butyryl)-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester

(2S,4R)-1-((2S,3R)-2-{(S)-5-[((2S,4S)-4-Azido-pyrrolidine-2-carbonyl)-amino]-2-[(4''-pentyloxy-[1,1';4',1'']terphenyl-4-carbonyl)-amino]-pentanoylamino}-3-tert-butoxy-butyryl)-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester