Phosphonic acid, [4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-hydroxy-5-(2-phenyl-4-oxazolyl )-6-heptenyl]-, dimethyl ester

Base Information

• Chemical Name: Phosphonic acid, [4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-hydroxy-5-(2-phenyl-4-oxazolyl )-6-heptenyl]-, dimethyl ester
• CAS No.: 142075-66-9
• Molecular Formula: C₂₄H₃₈NO₆PSi
• Molecular Weight: 495.628
• Mol file: 142075-66-9.mol

Synonyms:

Chemical Property of Phosphonic acid, [4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-hydroxy-5-(2-phenyl-4-oxazolyl )-6-heptenyl]-, dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphonic acid, [4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-hydroxy-5-(2-phenyl-4-oxazolyl )-6-heptenyl]-, dimethyl ester

There total 8 articles about Phosphonic acid, [4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-hydroxy-5-(2-phenyl-4-oxazolyl )-6-heptenyl]-, dimethyl ester 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: 80.0%

dimethyl lithiomethylphosphonate (34939-91-8,58648-56-9) + (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-phenyl-oxazol-4-yl)-hex-5-enal → [(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5-(2-phenyl-oxazol-4-yl)-hept-6-enyl]-phosphonic acid dimethyl ester (142075-66-9)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)79046-0

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → [(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5-(2-phenyl-oxazol-4-yl)-hept-6-enyl]-phosphonic acid dimethyl ester (142075-66-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) Et₃N, 2) DIBAL / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 deg C

2: 65 percent / TiCl₄, Zn / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

3: 95 percent / 2,3-dichloro-5,6-dicyanoquinone / benzene / Heating

4: 90 percent / HF, pyridine

5: 98 percent / Dess-Martin oxidation

6: 80 percent / tetrahydrofuran

With pyridine; hydrogen fluoride; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)79046-0

Reference yield:

2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline (102614-13-1) → [(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5-(2-phenyl-oxazol-4-yl)-hept-6-enyl]-phosphonic acid dimethyl ester (142075-66-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) LiNEt₂ / 1) THF, -78 deg C, 2) -78 deg C

2: 1) Et₃N, 2) DIBAL / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 deg C

3: 65 percent / TiCl₄, Zn / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

4: 95 percent / 2,3-dichloro-5,6-dicyanoquinone / benzene / Heating

5: 90 percent / HF, pyridine

6: 98 percent / Dess-Martin oxidation

7: 80 percent / tetrahydrofuran

With pyridine; hydrogen fluoride; lithium diethylamide; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)79046-0

upstream raw materials:

dimethyl lithiomethylphosphonate

t-butyldimethylsiyl triflate

2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline

(2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanethioic acid S-tert-butyl ester

Downstream raw materials:

C₂₄H₃₈NO₈PSi