N-ALFA-FMOC-4-(PHOSPHONODIFLUOROMETHYL)-L-PHENYLALANINE

Base Information

• Chemical Name: N-ALFA-FMOC-4-(PHOSPHONODIFLUOROMETHYL)-L-PHENYLALANINE
• CAS No.: 160751-44-0
• Molecular Formula: C25H22F2NO7P
• Molecular Weight: 517.423
• Mol file: 160751-44-0.mol

Synonyms:4-[(DITHYLPHOSPHONO)DIFLUOROMETHYL]-N-(FLUOREN-9-YLMETHOXYCARBONYL)-L-PHENYLALAMINE; Fmoc-4-(phosphonodifluoromethyl)phenylalanine; (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[difluoro(phosphono)methyl]phenyl}propanoic acid; 4-(DIETHYLPHOSPHONO)DIFLUOROMETHYL)-N-(FLUOREN-9-YL-METHOXYCARBONY)-L-PHENYLALANINE; 4-(DIFLUOROPHOSPHONOMETHYL)-N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-L-PHENYLALANINE; N-ALFA-FLUORENYLCARBONYL-4-(DIETHYLPHOSPHONODIFLUOROMETHYL)-L-PHENYLALANINE; Fmoc-F2Pmp-OH; (4-(DIETHYLPHOSPHONO)DIFLUOROMETHYL)-N-(FLUOREN-9-YL-METHOXYCARBONYL)-L-PHENYLALANINE; 查看更多英文别名 收起

Chemical Property of N-ALFA-FMOC-4-(PHOSPHONODIFLUOROMETHYL)-L-PHENYLALANINE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 721.4oC at 760mmHg
• PKA: 1.07±0.10(Predicted)
• Flash Point: 390.1oC
• PSA: 142.97000
• Density: 1.476 g/cm³
• LogP: 4.83890

Purity/Quality:

97% ^*data from raw suppliers

4-(Difluorophosphonomethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(Difluorophosphonomethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine is used as a reactant in the synthesis of small molecule PTP1B inhibitors of insulin signaling.

Technology Process of N-ALFA-FMOC-4-(PHOSPHONODIFLUOROMETHYL)-L-PHENYLALANINE

There total 9 articles about N-ALFA-FMOC-4-(PHOSPHONODIFLUOROMETHYL)-L-PHENYLALANINE 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:

(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid (156017-45-7) → (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[difluoro(phosphono)methyl]phenyl}propanoic acid (160751-44-0)

Guidance literature:

With bis(trimethylsilyl)trifluoroacetamide; trimethylsilyl iodide; In dichloromethane; at -20 - 20 ℃;

DOI:10.1021/jo9517508

Reference yield:

4-bromomethylbenzoic Acid (6232-88-8) → (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[difluoro(phosphono)methyl]phenyl}propanoic acid (160751-44-0)

Guidance literature:

Multi-step reaction with 7 steps

1: phosphorus tribromide / 3 h / Heating

2: 1.9 g / toluene / 0.67 h / 0 °C

3: 52 percent / (diethylamido)sulfur trifluoride / Ambient temperature

4: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C

5: 100 percent / H₂ / PdCl₂ / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr

6: 1.29 g / NaHCO₃ / H₂O; dioxane / 3 h / Ambient temperature

7: 1.19 g / bis(trimethylsilyl)trifluoroacetamide, iodotrimethylsilane / CH₂Cl₂ / -20 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; bis(trimethylsilyl)trifluoroacetamide; trimethylsilyl iodide; (diethylamido)sulfur trifluoride; hydrogen; phosphorus tribromide; sodium hydrogencarbonate; lithium hexamethyldisilazane; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; toluene;

DOI:10.1021/jo9517508

Reference yield:

4-(bromomethyl)benzoyl bromide (876-07-3) → (S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[difluoro(phosphono)methyl]phenyl}propanoic acid (160751-44-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.9 g / toluene / 0.67 h / 0 °C

2: 52 percent / (diethylamido)sulfur trifluoride / Ambient temperature

3: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C

4: 100 percent / H₂ / PdCl₂ / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr

5: 1.29 g / NaHCO₃ / H₂O; dioxane / 3 h / Ambient temperature

6: 1.19 g / bis(trimethylsilyl)trifluoroacetamide, iodotrimethylsilane / CH₂Cl₂ / -20 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; bis(trimethylsilyl)trifluoroacetamide; trimethylsilyl iodide; (diethylamido)sulfur trifluoride; hydrogen; sodium hydrogencarbonate; lithium hexamethyldisilazane; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; toluene;

DOI:10.1021/jo9517508

upstream raw materials:

(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid

4-bromomethylbenzoic Acid

4-(bromomethyl)benzoyl bromide

diethyl ((4-(α-bromomethyl)phenyl)oxomethyl)phosphonate

Downstream raw materials:

C₃₆H₅₄F₂N₁₁O₁₆P

C₃₄H₄₈F₂N₇O₁₆P

C₄₂H₄₅BrF₂IN₆O₁₁P

C₃₀H₃₁BrF₂IN₄O₇P

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