FMOC-S-DIPHENYLMETHYL-L-CYSTEINE

Base Information

• Chemical Name: FMOC-S-DIPHENYLMETHYL-L-CYSTEINE
• CAS No.: 247595-29-5
• Molecular Formula: C31H27NO4S
• Molecular Weight: 509.62
• Mol file: 247595-29-5.mol

Synonyms:FMOC-S-DIPHENYLMETHYL-L-CYSTEINE;Fmoc-Cys(Dpm)-OH;S-(Diphenylmethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cysteine

Chemical Property of FMOC-S-DIPHENYLMETHYL-L-CYSTEINE

Chemical Property:

• Boiling Point: 714.3±60.0 °C(Predicted)
• PKA: 3.43±0.10(Predicted)
• PSA: 100.93000
• Density: 1.281±0.06 g/cm3(Predicted)
• LogP: 6.89200
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

≥98%, ^*data from raw suppliers

Fmoc-Cys(Dpm)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of FMOC-S-DIPHENYLMETHYL-L-CYSTEINE

There total 2 articles about FMOC-S-DIPHENYLMETHYL-L-CYSTEINE 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: 78.0%

1,1-Diphenylmethanol (91-01-0) + Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine (135248-89-4) → Fmoc-L-Cys(Dpm)-OH (247595-29-5)

Guidance literature:

With trifluoroacetic acid; at 25 ℃; for 1h;

DOI:10.1021/ol302550p DOI:10.1021/ol302550p

Reference yield:

N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4) → Fmoc-L-Cys(Dpm)-OH (247595-29-5)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid; chlorotriisopropylsilane / dichloromethane / 0.5 h / 25 °C

2: trifluoroacetic acid / 1 h / 25 °C

With chlorotriisopropylsilane; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ol302550p DOI:10.1021/ol302550p

Reference yield: 66.0%

4-pentynoic acid (6089-09-4) + Fmoc-L-Cys(Dpm)-OH (247595-29-5) → C21H22N2O2S

Guidance literature:

Fmoc-L-Cys(Dpm)-OH; With piperidine; ethyl cyanoglyoxylate-2-oxime; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; for 1h;

4-pentynoic acid; In N,N-dimethyl-formamide; for 2h;

With trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/d0cc07463b

upstream raw materials:

1,1-Diphenylmethanol

N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine

N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine

Downstream raw materials:

Fmoc-Ala-L-Cys(Dpm)-Leu-NH₂

H-Gly-L-Cys-Phe-NH₂

Refernces

• 1、 Góngora-Benítez, Miriam,Mendive-Tapia, Lorena,Ramos-Tomillero, Iván,Breman, Arjen C.,Tulla-Puche, Judit,Albericio, Fernando. "Acid-labile cys-protecting groups for the Fmoc/tBu strategy: Filling the gap". supporting information. p. 5472 - 5475. Retrieved 2013/01/15.