FMOC-DOPA(ACETONIDE)-OH

Base Information

• Chemical Name: FMOC-DOPA(ACETONIDE)-OH
• CAS No.: 852288-18-7
• Molecular Formula: C27H25NO6
• Molecular Weight: 459.499
• Mol file: 852288-18-7.mol

Synonyms:(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((diphenyl(p-tolyl)methyl)amino)hexanoic acid;Fmoc-D-Lys(Mtt)-OH;

Chemical Property of FMOC-DOPA(ACETONIDE)-OH

Chemical Property:

• Boiling Point: 663.072 °C at 760 mmHg
• PKA: 3.68±0.10(Predicted)
• Flash Point: 354.814 °C
• PSA: 94.09000
• Density: 1.302g/cm³
• LogP: 5.11920
• Storage Temp.: Store at 0°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-Dopa(acetonide)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of FMOC-DOPA(ACETONIDE)-OH

There total 11 articles about FMOC-DOPA(ACETONIDE)-OH 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: 74.0%

H-DOPA(acetonide)-OH + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (2S)-3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid (852288-18-7)

Guidance literature:

In tetrahydrofuran; water; at 0 ℃; for 2h;

DOI:10.1016/j.tetlet.2008.07.052

Reference yield:

2,2-dimethoxy-propane (77-76-9) + N-(9-fluorenylmethyloxycarbonyl)-3,4-dihydroxy-L-phenylalanine (137018-93-0) → (2S)-3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid (852288-18-7)

Guidance literature:

In toluene; at 80 ℃; for 0.416667h; under 225.023 Torr; Temperature; Reagent/catalyst; Solvent; Pressure; Inert atmosphere; Sealed tube; Molecular sieve;

Reference yield:

levodopa (59-92-7,90638-38-3) → (2S)-3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid (852288-18-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / methanol / 20 °C

2.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 20 °C

3.1: toluene-4-sulfonic acid / benzene / 1 - 2 h / Reflux

4.1: lithium hydroxide / water; tetrahydrofuran / 2.5 h / Cooling with ice

5.1: water; tetrahydrofuran / 2 h / 0 °C / Cooling with ice

5.2: pH 2 - 3

With potassium hydrogencarbonate; triethylamine; lithium hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; benzene;

upstream raw materials:

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

levodopa

(2S)-3-(3,4-dihydroxyphenyl)-2-(2,2,2-trifluoroacetamido)propanoic acid

N-phthalimide-3,4-dihydroxy-L-phenylalanine methyl ester

Downstream raw materials:

levodopa

Refernces

• 1、 -. "Method of synthesizing acetonide-protected catechol-containing compounds and intermediates produced therein". Page/Page column 18-19; 20. . Retrieved 2012/07/30.
• 2、 Liu, Zhongqiang,Hu, Bi-Huang,Messersmith, Phillip B.. "Convenient synthesis of acetonide-protected 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis". . p. 5519 - 5521. Retrieved 2008/12/22.