ChemicalBook > CAS DataBase List > Fmoc-O-(benzylphospho)-L-threonine

Fmoc-O-(benzylphospho)-L-threonine

Product Name
Fmoc-O-(benzylphospho)-L-threonine
CAS No.
175291-56-2
Chemical Name
Fmoc-O-(benzylphospho)-L-threonine
Synonyms
FMOC-THR(HPO3BZL)-OH;L-PHOSPHOTHREONINE;Fmoc-L-Thr(HPO3Bzl)-OH;FMOC-THR(PO(OBZL)OH)-OH;Fl332-1;Fmoc-pThr(Bn)-OH;Fmoc-Thr(HP03Bzl)-OH;Fmoc-Thr(PO3BzlH)-OH;Fmoc-Thr(HPO?Bzl)-OH;FMOC-L-THR(PO(OBZL)OH)
CBNumber
CB4322287
Molecular Formula
C26H26NO8P
Formula Weight
511.46
MOL File
175291-56-2.mol
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Fmoc-O-(benzylphospho)-L-threonine Property

Density 
1.377±0.06 g/cm3(Predicted)
storage temp. 
Inert atmosphere,2-8°C
solubility 
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
pka
1.42±0.50(Predicted)
form 
Solid
color 
White to off-white
Sensitive 
Moisture Sensitive
InChIKey
HOFDVXHILSPFNS-OSPHWJPCSA-N
SMILES
C(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)(=O)N[C@H](C(O)=O)[C@@H](C)OP(=O)(O)OCC1=CC=CC=C1
CAS DataBase Reference
175291-56-2(CAS DataBase Reference)
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Safety

WGK Germany 
3
F 
10-21
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Usbiological
Product number
277026
Product name
Fmoc-O-benzylphospho-L-threonine
Packaging
250mg
Price
$336
Updated
2021/12/16
TRC
Product number
F647625
Product name
Fmoc-O-(Benzylphospho)-L-threonine
Packaging
250mg
Price
$145
Updated
2021/12/16
AK Scientific
Product number
M504
Product name
Fmoc-O-(Benzylphospho)-L-threonine
Packaging
250mg
Price
$147
Updated
2021/12/16
Activate Scientific
Product number
AS89247
Product name
Fmoc-O-(benzylphospho)-L-threonine
Purity
95% ee
Packaging
1g
Price
$180
Updated
2021/12/16
Matrix Scientific
Product number
094151
Product name
Fmoc-O-(benzylphospho)-L-threonine
Purity
95+%
Packaging
250mg
Price
$189
Updated
2021/12/16
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Fmoc-O-(benzylphospho)-L-threonine Chemical Properties,Usage,Production

Chemical Properties

White to off-white powder

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)

Uses

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.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

73731-37-0

100-51-6

175291-56-2

The general procedure for the synthesis of (2S,3R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoic acid from (2S,3R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((benzyloxy)(hydroxy)phosphono)oxy)butanoic acid with benzyl alcohol was as follows: 1. Raw material pretreatment: Dry the amino-protected amino acid (hydrated form) to a moisture content of <0.5% by weight. Weigh the dried amino-protected amino acids (1.0 equiv.) into a reaction flask. Anhydrous THF (4 volumes, EMD OmniSolv HPLC grade, >99.99%) was added and the total volume was labeled outside the flask. The mixture was heated to 70 °C and approximately 2 volumes of THF were removed by distillation at 700 mbar. the mixture was replenished to the original labeled volume with dry THF and this distillation and dilution process was repeated twice. The final water content of the amino acid solution was confirmed to be <0.20% by weight by Karl-Fischer titration. 2. Dichlorophosphite preparation: THF (8 volumes) was added to the flask under nitrogen protection and cooled to 0°C. PCl3 (1.30 equiv, Aldrich, Reagent Plus grade, 99%) was added slowly, keeping the reaction temperature at 0-5 °C. Pyridine (1 equiv, Aldrich, anhydrous, 99+%) was optionally added to maintain the reaction temperature at -5 to 5 °C. Benzyl alcohol (1.50 equiv, Aldrich, ACS grade, 99+%) was then added to maintain the temperature at -5 to 5 °C. The reaction mixture was stirred at 0-5 °C for 5 min and complete consumption of PCl3 was confirmed by 31P NMR. 2,6-Dimethylpyridine (3.00 equiv, Aldrich, >99%) was added and the reaction temperature was maintained at -5 to 5 °C to form a thick slurry. 3. Phosphite Intermediate Preparation: 2,6-dimethylpyridine (1.0 eq.) was added to a dry aminoprotected amino acid solution. This solution was slowly added to the mixture from Step 1, keeping the reaction temperature at -5 to 5°C. Rinse the flask with additional THF (1 volume) to ensure complete transfer. HPLC analysis (Method 1) was performed at 10-min intervals for 5 min after the start of the reaction until the ratio of APG-AA to the intermediate phosphite was stabilized. 4. Hydrolysis: After confirming that the reaction was complete, H2O (3.6 vol) was added slowly, keeping the reaction temperature at no more than 10°C to form a two-phase solution. 5. Oxidation: Add NaBr (2.32 eq., Aldrich, ACS grade, 99+%) and aqueous NaBrO3 (20 wt. %, 0.48 eq., Riedel-de-Haen, puriss grade, 98%) to the two-phase mixture, keeping the reaction at 0-5 °C. After completion of oxidation, the reaction was allowed to warm up slowly to room temperature, avoiding exceeding 30°C. The content of phosphite intermediates was confirmed to be <1.5% by HPLC. Finally, the reaction was terminated by a one-time addition of Na2S2O5 aqueous solution (10 wt%, 1 volume, Sigma-Aldrich, ACS grade, 97+%). Product characterization: 1H NMR, 13C NMR, 31P NMR and HRMS data were structurally consistent with the target compound with a specific rotation of +5.99°.

References

[1] Patent: WO2013/12416, 2013, A1. Location in patent: Page/Page column 70-71; 75

Fmoc-O-(benzylphospho)-L-threonine Preparation Products And Raw materials

Raw materials

Preparation Products

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Fmoc-O-(benzylphospho)-L-threonine Suppliers

China 165 Germany 4 India 2 Japan 3 South Korea 1 Switzerland 1 United Kingdom 4 United States 27 Global 207
SANBEM Biotech (Suzhou) Co., Ltd.
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View Lastest Price from Fmoc-O-(benzylphospho)-L-threonine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Fmoc-O-(benzylphospho)-L-threonine 175291-56-2
Price
US $0.00/KG
Min. Order
1KG
Purity
98.0%
Supply Ability
1kg/month
Release date
2023-01-09
Career Henan Chemical Co
Product
Fmoc-O-(benzylphospho)-L-threonine 175291-56-2
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20kg
Release date
2018-08-15
Career Henan Chemical Co
Product
Fmoc-O-(benzylphospho)-L-threonine 175291-56-2
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20kg
Release date
2018-08-15

175291-56-2, Fmoc-O-(benzylphospho)-L-threonineRelated Search:

L-Threonine Fmoc-Lys(Boc)-OH Dibenzyl phosphate Benzyltriethylammonium chloride FMOC-TYR(PO(OBZL)OH)-OH 9-Fluorenylmethyl chloroformate Nalpha-Fmoc-Ndelta-trityl-L-glutamine Fmoc-O-(benzylphospho)-L-serine Fmoc-Phe-OH Benzyl chloride 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butanoic acid Benzyl chloroformate CHLOROPHOSPHONAZO III Benzyl benzoate Fmoc-OSu FMOC-THR(TBU)-OL FMOC-SER(PO3H2)-OH O-Phospho-L-serine

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  • Amino Acid Derivatives
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