2-(((9H-Fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoic acid

Base Information

• Chemical Name: 2-(((9H-Fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoic acid
• CAS No.: 1068435-19-7
• Molecular Formula: C27H31NO4
• Molecular Weight: 433.54
• Hs Code.: 2924299090
• Mol file: 1068435-19-7.mol

Synonyms:6-Heptenoic acid, 2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2-(4-penten-1-yl)-;2-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-pent-4-enyl-hept-6-enoic acid;

Chemical Property of 2-(((9H-Fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoic acid

Chemical Property:

• Boiling Point: 638.26 °C at 760 mmHg
• PKA: 3.87±0.50(Predicted)
• Flash Point: 339.808 °C
• PSA: 75.63000
• Density: 1.137 g/cm³
• LogP: 6.45200
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

2-?((((9H-?Fluoren-?9-?yl)?methoxy)?carbonyl)?amino)?-?2-?(pent-?4-?en-?1-?yl)?hept-?6-?enoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-?((((9H-?Fluoren-?9-?yl)?methoxy)?carbonyl)?amino)?-?2-?(pent-?4-?en-?1-?yl)?hept-?6-?enoic Acid can be used in preparation of peptidomimetic macrocycles useful in treatment of solid tumors.

Technology Process of 2-(((9H-Fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoic acid

There total 6 articles about 2-(((9H-Fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoic 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: 78.0%

ethyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoate (1068436-20-3) → 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoic acid (1068435-19-7)

Guidance literature:

With aluminum tri-bromide; dimethylsulfide; In dichloromethane; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ja505141j

Reference yield:

2,2-bis(4-pentenyl)glycine + 9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) → 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoic acid (1068435-19-7)

Guidance literature:

2,2-bis(4-pentenyl)glycine; With edetate disodium; sodium carbonate; In water; for 0.166667h; pH=9 - 10;

9-fluorenylmethyl N-succinimidyl carbonate; In water; acetonitrile; at -10 - 20 ℃; for 15h;

DOI:10.1016/j.tetlet.2017.05.007

Reference yield:

1-iodo-4-pentene (7766-48-5) → 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoic acid (1068435-19-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: hydrogenchloride / diethyl ether; water / 1 h / 0 - 20 °C / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

3.1: aluminum tri-bromide; dimethylsulfide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; aluminum tri-bromide; dimethylsulfide; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1021/ja505141j

upstream raw materials:

ethyl 2-(diphenylmethyleneamino)-2-(pent-4-enyl)hept-6-enoate

1-iodo-4-pentene

ethyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(pent-4-enyl)hept-6-enoate

bromopentene

Refernces

• 1、 -. "STITCHED POLYPEPTIDES". . . Retrieved 2017/01/02.