Fmoc-D-Thr(Po(Obzl)Oh)-OH

Base Information

• Chemical Name: Fmoc-D-Thr(Po(Obzl)Oh)-OH
• CAS No.: 175291-56-2
• Molecular Formula: C26H26NO8P
• Molecular Weight: 511.468
• DSSTox Substance ID: DTXSID90938646
• Wikidata: Q72478085
• Mol file: 175291-56-2.mol

Synonyms:Fmoc-D-Thr(Po(Obzl)Oh)-OH;937171-63-6;Fmoc-O-benzyl-L-phosphothreonine;Fmoc-Thr(PO3BzlH)-OH;(2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[hydroxy(phenylmethoxy)phosphoryl]oxybutanoic acid;(2R,3S)-3-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoic acid;Fmoc-Thr{PO(OBzl)OH}-OH;SCHEMBL15630872;DTXSID90938646;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-((benzyloxy)(hydroxy)phosphoryl)-L-threonine;MFCD07363481;AM84618;HY-W142100;CS-0201884;E70766;J-011104;O-[(Benzyloxy)(hydroxy)phosphoryl]-N-{[(9H-fluoren-9-yl)methoxy](hydroxy)methylidene}threonine

Chemical Property of Fmoc-D-Thr(Po(Obzl)Oh)-OH

Chemical Property:

• Refractive Index: 1.614
• PKA: 1.42±0.50(Predicted)
• PSA: 141.20000
• Density: 1.377 g/cm³
• LogP: 5.09150
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 511.13960379
• Heavy Atom Count: 36
• Complexity: 781

Purity/Quality:

99%, ^*data from raw suppliers

Fmoc-O-benzylphospho-L-threonine ^*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: CC(C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OP(=O)(O)OCC4=CC=CC=C4
• Isomeric SMILES: C[C@@H]([C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OP(=O)(O)OCC4=CC=CC=C4
• Uses: Building block for the synthesis of phosphothreonine containing peptides. T.Wakamiya et al., Chem. Lett. , 1994, 1099 T.Vorherr and W.Bannwarth, Bioorg. Med. Chem. Lett 5, 2661 (1995) Fmoc-O-(Benzylphospho)-L-threonine, is a synthetic peptide used in the synthesis of macrocyclic peptidomimetics as pololike kinase 1 polo-box domain-binding inhibitors.

Technology Process of Fmoc-D-Thr(Po(Obzl)Oh)-OH

There total 12 articles about Fmoc-D-Thr(Po(Obzl)Oh)-OH 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: 86.0%

(2S,3R)-3-[Benzyloxy-(2,2,2-trichloro-ethoxy)-phosphoryloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester (175291-55-1) → Fmoc-L-Thr(HPO3Bzl)-OH (175291-56-2)

Guidance literature:

With acetic acid; zinc; for 1.5h;

DOI:10.1246/bcsj.69.465

Reference yield: 67.0%

Fmoc-Thr-OH (73731-37-0) + benzyl alcohol (100-51-6,185532-71-2) → Fmoc-L-Thr(HPO3Bzl)-OH (175291-56-2)

Guidance literature:

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

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

Reference yield:

C26H26NO7P → Fmoc-L-Thr(HPO3Bzl)-OH (175291-56-2)

Guidance literature:

With sodium bromate; sodium bromide; at 0 - 5 ℃; for 2.5h;

upstream raw materials:

(2S,3R)-3-[Benzyloxy-(2,2,2-trichloro-ethoxy)-phosphoryloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

Fmoc-Thr-OH

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

N-(9-fluorenylmethyloxycarbonyl)-L-threonine phenacylester

Downstream raw materials:

C₆₇H₁₀₂N₁₉O₁₉PS₃

Refernces

• 1、 -. "PROCESS FOR PREPARING PHOSPHORYLATED AMINO ACIDS". Page/Page column 78; 82. . Retrieved 2013/03/26.
• 2、 Wakamiya, Tateaki,Nishida, Takatoshi,Togashi, Ryusaku,Saruta, Kunio,Yasuoka, Jun-Ichi,Kusumoto, Shoichi. "Preparations of Nα-Fmoc-O-[(benzyloxy)hydroxyphosphinyl] β-hydroxy α-amino acid derivatives". . p. 465 - 468. Retrieved 2007/10/03.