(S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate

Base Information

• Chemical Name: (S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate
• CAS No.: 935548-32-6
• Molecular Formula: C₃₆H₅₄F₃N₂O₇P
• Molecular Weight: 714.803
• Mol file: 935548-32-6.mol

Synonyms:(S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate

Chemical Property of (S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate

There total 4 articles about (S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate 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: 99.0%

(S)-methyl 2-palmitamido-3-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)propanoate (935548-14-4) + dimethyl methane phosphonate (756-79-6) → (S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate (935548-32-6)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

(S)-methyl 2-palmitamido-3-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)propanoate; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.bmcl.2010.09.030

Reference yield:

L-tyrosine methyl ester HCl (3417-91-2) → (S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate (935548-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N / CH₂Cl₂ / 3 h / 0 °C

2.1: K₂CO₃; 18-crown-6 / acetone / Heating

3.1: n-BuLi

3.2: 3 h / -78 °C

With n-butyllithium; 18-crown-6 ether; potassium carbonate; triethylamine; In dichloromethane; acetone;

DOI:10.1016/j.bmcl.2006.12.114

Reference yield:

n-hexadecanoyl chloride (112-67-4) → (S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate (935548-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N / CH₂Cl₂ / 3 h / 0 °C

2.1: K₂CO₃; 18-crown-6 / acetone / Heating

3.1: n-BuLi

3.2: 3 h / -78 °C

With n-butyllithium; 18-crown-6 ether; potassium carbonate; triethylamine; In dichloromethane; acetone;

DOI:10.1016/j.bmcl.2006.12.114

upstream raw materials:

(S)-methyl 2-palmitamido-3-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)propanoate

dimethyl methane phosphonate

L-tyrosine methyl ester HCl

n-hexadecanoyl chloride

Downstream raw materials:

dimethyl (3S)-2-hydroxy-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate

dimethyl (3S)-2-hydroxy-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate

Refernces

• 1、 Cui, Peng,Tomsig, Jose L.,McCalmont, William F.,Lee, Sangderk,Becker, Christopher J.,Lynch, Kevin R.,Macdonald, Timothy L.. "Synthesis and biological evaluation of phosphonate derivatives as autotaxin (ATX) inhibitors". . p. 1634 - 1640. Retrieved 2007/10/03.