FMOC-ASP(OMPE)-OH

Base Information

• Chemical Name: FMOC-ASP(OMPE)-OH
• CAS No.: 180675-08-5
• Molecular Formula: C₂₅H₂₉NO₆
• Molecular Weight: 439.508
• Mol file: 180675-08-5.mol

Synonyms:FMOC-ASPARTIC ACID(OMPE);FMOC-ASP(OMPE)-OH;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-ASPARTIC ACID 3-METHYL-PENT-3-YL;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-ASPARTIC ACID 3-METHYLPENTYL ESTER;N-ALPHA-FMOC-(O-3-METHYL-PENT-3-YL)ASPARTIC ACID

Chemical Property of FMOC-ASP(OMPE)-OH

Chemical Property:

• Boiling Point: 635.9±55.0 °C(Predicted)
• PKA: 3.56±0.23(Predicted)
• PSA: 105.42000
• Density: 1.214±0.06 g/cm3(Predicted)
• LogP: 4.69470
• Storage Temp.: -15°C

Purity/Quality:

99.3% ^*data from raw suppliers

Fmoc-asp(ompe)-oh ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: The side chain protecting group Mpe in Fmoc-Asp(OMpe)-OH is a more bulky group than the standard tert-Butyl (tBu) group, which significantly helps suppressing the notorious side reaction of aspartimide formation, and thus improve the purity of the crude peptide and facility the time- and cost-intensive purification as well.
• Uses: FMOC-ASP(OMPE)-OH can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Technology Process of FMOC-ASP(OMPE)-OH

There total 8 articles about FMOC-ASP(OMPE)-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: 81.0%

Fmoc-D-Asp(Mpe)-OBn → Fmoc-D-Asp(Mpe)-OH (180675-08-5,1926162-97-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; for 0.333333h; Inert atmosphere;

DOI:10.1021/jacs.7b02988

Reference yield:

3-methylpentan-3-ol (77-74-7) → FmocHN-Asp(OMpe)-COOH (180675-08-5,1926162-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 1 h / 50 °C

2: hydrogen / Pd

With hydrogen; palladium; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00807-6

Reference yield:

N-(9-fluorenylmethoxycarbonyl)-L-aspartyl α-benzyl ester (86060-83-5) → FmocHN-Asp(OMpe)-COOH (180675-08-5,1926162-97-1)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride / tetrahydrofuran

2: tetrahydrofuran / 1 h / 50 °C

3: hydrogen / Pd

With oxalyl dichloride; hydrogen; palladium; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00807-6

upstream raw materials:

3-methylpentan-3-ol

N-(9-fluorenylmethoxycarbonyl)-L-aspartyl α-benzyl ester

(S)-3-Chlorocarbonyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester

N-(9-fluorenylmethoxycarbonyl)-4-O-tert-butyl-D-aspartic acid

Downstream raw materials:

human C-type natriuretic peptide 22

L-3-aminosuccinimide

Refernces

• 1、 Karlstroem, Amelie,Unden, Anders. "A new protecting group for aspartic acid that minimizes piperidine-catalyzed aspartimide formation in fmoc solid phase peptide synthesis". . p. 4243 - 4246. Retrieved 2007/10/03.