Fmoc-3,4-dihydroxy-L-phenylalanine

Base Information

• Chemical Name: Fmoc-3,4-dihydroxy-L-phenylalanine
• CAS No.: 137018-93-0
• Molecular Formula: C24H21NO6
• Molecular Weight: 419.434
• Hs Code.: 2924299090
• European Community (EC) Number: 856-765-3
• Nikkaji Number: J1.222.138J
• Mol file: 137018-93-0.mol

Synonyms:Fmoc-3,4-dihydroxy-L-phenylalanine;137018-93-0;L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-hydroxy-;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoic acid;(2S)-3-(3,4-dihydroxyphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;SCHEMBL9732381;fmoc-3,4-dihydroxy-phenylalanine;AKOS012614494;AKOS015837225;CS-0169347;EN300-81252;Z1123720072;(2S)-3-(3,4-dihydroxyphenyl)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoicacid

Chemical Property of Fmoc-3,4-dihydroxy-L-phenylalanine

Chemical Property:

• Boiling Point: 714.2±60.0 °C(Predicted)
• PKA: 2.95±0.10(Predicted)
• PSA: 119.58000
• Density: 1.396±0.06 g/cm3(Predicted)
• LogP: 3.83660
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 419.13688739
• Heavy Atom Count: 31
• Complexity: 620

Purity/Quality:

98%min ^*data from raw suppliers

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC(=C(C=C4)O)O)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC(=C(C=C4)O)O)C(=O)O

Technology Process of Fmoc-3,4-dihydroxy-L-phenylalanine

There total 4 articles about Fmoc-3,4-dihydroxy-L-phenylalanine 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: 95.0%

levodopa (59-92-7,90638-38-3) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-(9-fluorenylmethyloxycarbonyl)-3,4-dihydroxy-L-phenylalanine (137018-93-0)

Guidance literature:

With sodium tetraborate decahydrate; sodium carbonate; In tetrahydrofuran; water; at 20 ℃; for 4h; Inert atmosphere;

Reference yield: 68.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + β-3,4-dihydroxyphenyl-L-alanine hydrochloride (5796-14-5) → N-(9-fluorenylmethyloxycarbonyl)-3,4-dihydroxy-L-phenylalanine (137018-93-0)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 20 ℃;

DOI:10.1021/jm050910x

Reference yield: 64.6%

levodopa (59-92-7,90638-38-3) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-(9-fluorenylmethyloxycarbonyl)-3,4-dihydroxy-L-phenylalanine (137018-93-0)

Guidance literature:

levodopa; With sodium carbonate; In 1,4-dioxane; water; for 0.166667h;

(fluorenylmethoxy)carbonyl chloride; In 1,4-dioxane; water; for 29h;

DOI:10.1016/S0040-4020(01)00601-9

upstream raw materials:

levodopa

(fluorenylmethoxy)carbonyl chloride

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

β-3,4-dihydroxyphenyl-L-alanine hydrochloride

Downstream raw materials:

(S)-3-(3,4-bis-trityloxy-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid

(2S)-3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid

L-dopa-(NMe-Phe)4-CONH₂

3,4-dihydroxy-L-phenylalanyl-N-MePhe-N-MePhe-N-MePhe-CONH₂