O-Benzyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-N-phosphonotyrosine

Base Information

• Chemical Name: O-Benzyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-N-phosphonotyrosine
• CAS No.: 191348-16-0
• Molecular Formula: C31H28NO8P
• Molecular Weight: 573.539
• Hs Code.: 29224999
• DSSTox Substance ID: DTXSID20694066
• Mol file: 191348-16-0.mol

Synonyms:DTXSID20694066;FT-0653828;A813487;N-alpha-(9-Fuorenylmethyloxycarbonyl)-2-benzyl-l-phosphotyrosine;O-Benzyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-N-phosphonotyrosine;2-[[9H-fluoren-9-ylmethoxy(oxo)methyl]-phosphonoamino]-3-(4-phenylmethoxyphenyl)propanoic acid

Chemical Property of O-Benzyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-N-phosphonotyrosine

Chemical Property:

• Refractive Index: 1.638
• PKA: 1.37±0.50(Predicted)
• PSA: 141.20000
• Density: 1.378 g/cm³
• LogP: 6.30790
• Storage Temp.: -20°C
• Solubility.: Soluble in 0.1g in 2mL DMF.
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 573.15525385
• Heavy Atom Count: 41
• Complexity: 905

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC=C(C=C2)CC(C(=O)O)N(C(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)P(=O)(O)O
• Uses: N-Fmoc-O-benzylphospho-L-tyrosine is used as pharmaceutical intermediates.

Technology Process of O-Benzyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-N-phosphonotyrosine

There total 4 articles about O-Benzyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-N-phosphonotyrosine 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: 68.0%

→ (S)-3-[4-(Benzyloxy-hydroxy-phosphoryloxy)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (191348-16-0)

Guidance literature:

With phosphorus trichloride; In tetrahydrofuran; at -5 - 5 ℃; for 0.0833333h; Inert atmosphere;

With 2,6-dimethylpyridine; In tetrahydrofuran; at -5 - 5 ℃; Further stages; Inert atmosphere;

Reference yield:

benzyloxy dichlorophosphine (76101-29-6) + N-Fmoc-Tyr-OH (112883-29-1,92954-90-0) → (S)-3-[4-(Benzyloxy-hydroxy-phosphoryloxy)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (191348-16-0)

Guidance literature:

benzyloxy dichlorophosphine; With 2,6-dimethylpyridine; In tetrahydrofuran; at -5 - 5 ℃;

N-Fmoc-Tyr-OH; In tetrahydrofuran; at -5 - 5 ℃; Further stages;

DOI:10.1021/ol203332j

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (S)-3-[4-(Benzyloxy-hydroxy-phosphoryloxy)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (191348-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: phosphorus trichloride / tetrahydrofuran / 0 - 5 °C

2.1: 2,6-dimethylpyridine / tetrahydrofuran / -5 - 5 °C

2.2: -5 - 5 °C

With 2,6-dimethylpyridine; phosphorus trichloride; In tetrahydrofuran;

DOI:10.1021/ol203332j

upstream raw materials:

N²-<<(9H-Fluoren-9-yl)methoxy>carbonyl>-O⁴--L-tyrosine

benzyloxy dichlorophosphine

N-Fmoc-Tyr-OH

benzyl alcohol

Refernces

• 1、 -. "PROCESS FOR PREPARING PHOSPHORYLATED AMINO ACIDS". Page/Page column 82; 85. . Retrieved 2013/03/26.
• 2、 Kitas, Eric A.,Wade, John D.,Johns, R. B.,Perich, John W.,Tregear, Geoffrey W.. "Preparation and Use of Nα-Fluorenylmethoxycarbonyl-O-dibenzylphosphono-L-tyrosine in Continuous Flow Solid Phase Peptide Synthesis". . p. 338 - 339. Retrieved 2007/10/02.