Fmoc-Ser(tBu)-OPfp

Base Information

• Chemical Name: Fmoc-Ser(tBu)-OPfp
• CAS No.: 105751-13-1
• Molecular Formula: C28H24F5NO5
• Molecular Weight: 549.494
• Hs Code.: 29224999
• DSSTox Substance ID: DTXSID50457823
• Nikkaji Number: J1.151.346H
• Wikidata: Q72478762
• Mol file: 105751-13-1.mol

Synonyms:Fmoc-Ser(tBu)-OPfp;105751-13-1;(2,3,4,5,6-pentafluorophenyl) (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]propanoate;Fmoc-L-Ser(tBu)-OPfp;L-Serine,O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-,2,3,4,5,6-pentafluorophenyl ester;SCHEMBL8538000;DTXSID50457823;MFCD00062213;AKOS015853209;AKOS015904121;CS-W009605;HY-W008889;F10537;Fmoc-Ser(tBu)-OPfp, technical, >=90% (HPLC);J-001476;N-(9H-Fluorene-9-ylmethoxycarbonyl)-O-tert-butyl-L-serine pentafluorophenyl ester;N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-t-butyl-L-serine pentafluorphenol ester (Fmoc-L-Ser(tBu)-OPfp)

Chemical Property of Fmoc-Ser(tBu)-OPfp

Chemical Property:

• Vapor Pressure: 1.08E-15mmHg at 25°C
• Melting Point: 67-71℃
• Refractive Index: 1.545
• Boiling Point: 628.165 °C at 760 mmHg
• PKA: 9.82±0.46(Predicted)
• Flash Point: 333.702 °C
• PSA: 73.86000
• Density: 1.35 g/cm³
• LogP: 6.40080
• Storage Temp.: 2-8°C
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 549.15746368
• Heavy Atom Count: 39
• Complexity: 821

Purity/Quality:

98%Min ^*data from raw suppliers

Fmoc-Ser(tBu)-OPfp ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OCC(C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: CC(C)(C)OC[C@@H](C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: Fmoc-Ser(tBu)-OPfp is used as a reactant in the synthesis of peptides and peptide derivatives.

Technology Process of Fmoc-Ser(tBu)-OPfp

There total 4 articles about Fmoc-Ser(tBu)-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: 80.0%

Fmoc-Ser(tBu)-OH (71989-33-8) + pentafluorophenyl 4-nitrobenzenesulfonate (244633-31-6) → O-tert-butyl-Nα-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester (105751-13-1,244633-35-0)

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) + Fmoc-Ser(tBu)-OH (71989-33-8) → O-tert-butyl-Nα-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester (105751-13-1,244633-35-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; at 20 ℃; for 2h;

DOI:10.1021/ol062607b

Reference yield:

2,3,4,5,6-pentafluorophenol (771-61-9) → O-tert-butyl-Nα-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester (105751-13-1,244633-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / pyridine / 4 °C

2: 80 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:

(S)-O-tert-butylserine

(9-fluorenyl)methyl pentafluorophenyl carbonate

Fmoc-Ser(tBu)-OH

pentafluorophenyl 4-nitrobenzenesulfonate

Downstream raw materials:

Fmoc--Ser-O-Pfp

N-(9-fluorenylmethoxycarbonyl)-O⁽³⁾-tert-butyl-L-seryl-N-ethyl-S-triphenylmethyl-L-cysteine

N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-L-serine pentafluorophenyl ester

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester

Refernces

• 1、 Pudhom, Khanitha,Vilaivan, Tirayut. "Synthesis of aryl esters of protected amino acids from aryl sulfonates". . p. 5939 - 5942. Retrieved 2007/10/03.