Fmoc-L-homophenylalanine

Base Information

• Chemical Name: Fmoc-L-homophenylalanine
• CAS No.: 132684-59-4
• Molecular Formula: C25H23NO4
• Molecular Weight: 401.462
• Hs Code.: 2924 29 70
• European Community (EC) Number: 844-853-4
• DSSTox Substance ID: DTXSID20375787
• Nikkaji Number: J1.112.241H
• Wikidata: Q72478473
• Mol file: 132684-59-4.mol

Synonyms:Fmoc-L-homophenylalanine;NPC 14686;NPC-14686;NPC14686

Chemical Property of Fmoc-L-homophenylalanine

Chemical Property:

• Vapor Pressure: 1.19E-16mmHg at 25°C
• Melting Point: 141.0 to 145.0 °C
• Refractive Index: 1.624
• Boiling Point: 628.284 °C at 760 mmHg
• PKA: 3.84±0.10(Predicted)
• Flash Point: 333.774 °C
• PSA: 75.63000
• Density: 1.255 g/cm³
• LogP: 5.00200
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 401.16270821
• Heavy Atom Count: 30
• Complexity: 566

Purity/Quality:

≥99% ^*data from raw suppliers

Fmoc-L-homophenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-44-35-28-7-4

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)CC[C@@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: It is used as an active pharmaceutical intermediate.

Technology Process of Fmoc-L-homophenylalanine

There total 2 articles about Fmoc-L-homophenylalanine 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: 81.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + D-homophenylalanine (82795-51-5) → N-(fluorenyl-9-methoxycarbonyl)-L-homophenylalanine (132684-59-4,186320-01-4)

Guidance literature:

D-homophenylalanine; With sodium carbonate; In water; for 0.166667h; Cooling with ice;

(fluorenylmethoxy)carbonyl chloride; In 1,4-dioxane; water; for 12h;

DOI:10.1002/chem.202103071

Reference yield:

D-homophenylalanine (943-73-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-(fluorenyl-9-methoxycarbonyl)-L-homophenylalanine (132684-59-4,186320-01-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 18h;

DOI:10.1002/anie.202017086

Reference yield: 96.0%

pentafluorophenyl trifloroacetate (14533-84-7) + N-(fluorenyl-9-methoxycarbonyl)-L-homophenylalanine (132684-59-4,186320-01-4) → pentafluorophenyl L-α-[(9H-fluoren-9-ylmethoxycarbonyl)amino]benzenebutanoate (839719-69-6)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/jm049906w

upstream raw materials:

D-homophenylalanine

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

(fluorenylmethoxy)carbonyl chloride

D-homophenylalanine

Downstream raw materials:

H-Tyr-D-Orn[*]-Hfe-Asp[*]-NH₂