Fmoc-D-Glu(OtBu)-OPfp

Base Information

• Chemical Name: Fmoc-D-Glu(OtBu)-OPfp
• CAS No.: 200616-21-3
• Molecular Formula: C₃₀H₂₆F₅NO₆
• Molecular Weight: 591.532
• Mol file: 200616-21-3.mol

Synonyms:5-tert-Butyl 1-(pentafluorophenyl) N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-glutamate;D-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 5-(1,1-dimethylethyl) 1-(2,3,4,5,6-pentafluorophenyl) ester;

Chemical Property of Fmoc-D-Glu(OtBu)-OPfp

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.545
• Boiling Point: 674.204 °C at 760 mmHg
• PKA: 10.08±0.46(Predicted)
• Flash Point: 361.546 °C
• PSA: 90.93000
• Density: 1.353 g/cm³
• LogP: 6.70760
• Storage Temp.: Store at 0°C

Purity/Quality:

99%+, ^*data from raw suppliers

Fmoc-D-Glu(OtBu)-OPfp ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Fmoc-D-Glu(OtBu)-OPfp (cas# 200616-21-3) is glutamine derivative used in the patented preparation of liver retention clearing agents.

Technology Process of Fmoc-D-Glu(OtBu)-OPfp

There total 5 articles about Fmoc-D-Glu(OtBu)-OPfp 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: 85.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + Fmoc-Glu(OtBu)-OH (71989-18-9) → Nα-Fmoc-Glu-(O-tBu)-OPfp (86061-04-3,200616-21-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; 0 deg C, 1 h; r.t., 1 h;

DOI:10.1055/s-1983-30327

Reference yield: 61.0%

Fmoc-Glu(OtBu)-OH (71989-18-9) + pentafluorophenyl 4-nitrobenzenesulfonate (244633-31-6) → Nα-Fmoc-Glu-(O-tBu)-OPfp (86061-04-3,200616-21-3)

Guidance literature:

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0040-4039(99)01178-8

Reference yield:

2,3,4,5,6-pentafluorophenol (771-61-9) → Nα-Fmoc-Glu-(O-tBu)-OPfp (86061-04-3,200616-21-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / pyridine / 4 °C

2: 61 percent / HOBt; DIEA / dimethylformamide / 20 °C

With pyridine; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; 1: Esterification / 2: Esterification;

DOI:10.1016/S0040-4039(99)01178-8

upstream raw materials:

2,3,4,5,6-pentafluorophenol

Fmoc-Glu(OtBu)-OH

pentafluorophenyl 4-nitrobenzenesulfonate

L-glutamic acid 5-tert-butyl ester

Refernces

• 1、 Schoen, Istvan,Kisfaludy, Lajos. "9-Fluorenylmethyl Pentafluorophenyl Carbonate as a Useful Reagent for the Preparation of N-9-Fluorenylmethyloxycarbonylamino Acids and their Pentafluorophenyl Esters". . p. 303 - 305. Retrieved 2007/10/02.