Fmoc-O-(benzylphospho)-L-serine

Base Information

• Chemical Name: Fmoc-O-(benzylphospho)-L-serine
• CAS No.: 158171-14-3
• Molecular Formula: C25H24NO8P
• Molecular Weight: 497.441
• Hs Code.: 2924 29 70
• European Community (EC) Number: 822-879-7
• DSSTox Substance ID: DTXSID90451527
• Nikkaji Number: J3.060.254D
• Wikidata: Q72478081
• Mol file: 158171-14-3.mol

Synonyms:158171-14-3;Fmoc-O-(benzylphospho)-L-serine;Fmoc-Ser(HPO3Bzl)-OH;Fmoc-Ser(PO3BzlH)-OH;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[hydroxy(phenylmethoxy)phosphoryl]oxypropanoic acid;Fmoc-Ser(PO(OBzl)OH)-OH;Fmoc-Ser{PO(OBzl)OH}-OH;MFCD00797869;Fmoc-O-benzylphospho-L-serine;N-Fmoc-O-(benzylphospho)-L-serine;SCHEMBL12687031;DTXSID90451527;AKOS015895499;AM84517;CS-W018333;HY-W017617;L-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-[hydroxy(phenylmethoxy)phosphinyl]-;N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-((benzyloxy)(hydroxy)phosphoryl)-L-serine;AC-31998;AS-74012;F10661;Fmoc-Ser(PO3BzlH)-OH, >=97.0% (HPLC);Fmoc-O-[Hydroxy(benzyloxy)phosphinyl]-L-Ser-OH;A809903;Q-201132;N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-benzyl-L-phosphoserine;O-[(Benzyloxy)(hydroxy)phosphoryl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine;(2S)-2-[[9H-fluoren-9-ylmethoxy(oxo)methyl]amino]-3-[hydroxy(phenylmethoxy)phosphoryl]oxypropanoic acid;(2S)-3-{[(BENZYLOXY)(HYDROXY)PHOSPHORYL]OXY}-2-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)PROPANOIC ACID;(S)-3-(Benzyloxy-hydroxy-phosphoryloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

Chemical Property of Fmoc-O-(benzylphospho)-L-serine

Chemical Property:

• Appearance/Colour: white powder
• Refractive Index: 1.622
• PKA: 1.42±0.50(Predicted)
• PSA: 141.20000
• Density: 1.403 g/cm³
• LogP: 4.70300
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 497.12395372
• Heavy Atom Count: 35
• Complexity: 751

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-O-benzylphospho-L-serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COP(=O)(O)OCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)COP(=O)(O)OC[C@@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: Building block for the synthesis of phosphoserine containing peptides. It can be applied in the synthesis of phosphopeptides. This derivative can be introduced using standard activation methods, such as PyBOP and TBTU. The monoprotected phosphoserine residue once incorporated is stable to piperidine. Using this reagent, even peptides containing multiple phosphorylation sites can be prepared efficiently by standard Fmoc SPPS methods. β-piperidinylalanine formation has been shown to occur during Fmoc deprotection of N-terminal Ser(PO(OBzl)OH), particularly under microwave conditions. This side reaction can be eliminated by using cyclohexylamine or DBU just for this Fmoc deprotection step .

Technology Process of Fmoc-O-(benzylphospho)-L-serine

There total 11 articles about Fmoc-O-(benzylphospho)-L-serine 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: 80.9%

Fmoc-Ser-OPac (175291-54-0) → (S)-3-(Benzyloxy-hydroxy-phosphoryloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (158171-14-3)

Guidance literature:

With acetic acid; zinc; for 1.5h;

DOI:10.1246/bcsj.69.465

Reference yield: 54.5%

C25H22NO6P → (S)-3-(Benzyloxy-hydroxy-phosphoryloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (158171-14-3)

Guidance literature:

C₂₅H₂₂NO₆P; With water; at 5 ℃;

With sodium bromate; sodium bromide; at 0 - 20 ℃;

DOI:10.1021/op300233g

Reference yield:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → (S)-3-(Benzyloxy-hydroxy-phosphoryloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (158171-14-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) dicyclohexylamine, 2.) Et₃N / 1.) AcOEt, 2 h, 2.) DMF, RT, 3.5 h

2: 1H-tetrazole / tetrahydrofuran / 1.5 h / Ambient temperature

3: 80percent mCPBA / tetrahydrofuran / 0.67 h / 0 - 20 °C

4: 80.9 percent / 90percent aq. AcOH, Zn / 1.5 h

With 1H-tetrazole; acetic acid; triethylamine; N-cyclohexyl-cyclohexanamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran;

DOI:10.1246/bcsj.69.465

upstream raw materials:

Fmoc-Ser-OPac

N-Fmoc serine phenacyl ester

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

Downstream raw materials:

L-phosphoserine

C₇₂H₁₁₄N₂₅O₂₁P

C₇₁H₁₁₂N₂₅O₂₁P

Fmoc-O-benzyloxy-phosphono-L-serine cyclohexyl amide

Refernces

• 1、 -. "PROCESS FOR PREPARING PHOSPHORYLATED AMINO ACIDS". . . Retrieved 2013/03/26.
• 2、 Petrillo, Daniel E.,Mowrey, Dale R.,Allwein, Shawn P.,Bakale, Roger P.. "A general preparation of protected phosphoamino acids". supporting information; experimental part. p. 1206 - 1209. Retrieved 2012/05/04.