(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-8-(diisopropoxy-phosphoryl)-5-oxo-oct-6-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-8-(diisopropoxy-phosphoryl)-5-oxo-oct-6-enoic acid methyl ester
• CAS No.: 87118-72-7
• Molecular Formula: C₃₁H₄₅O₇PSi
• Molecular Weight: 588.753
• Mol file: 87118-72-7.mol

Synonyms:(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-8-(diisopropoxy-phosphoryl)-5-oxo-oct-6-enoic acid methyl ester

Chemical Property of (E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-8-(diisopropoxy-phosphoryl)-5-oxo-oct-6-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-8-(diisopropoxy-phosphoryl)-5-oxo-oct-6-enoic acid methyl ester

There total 10 articles about (E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-8-(diisopropoxy-phosphoryl)-5-oxo-oct-6-enoic acid methyl 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: 60.0%

(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{2-[(E)-3-(diisopropoxy-phosphoryl)-allyl]-[1,3]dioxolan-2-yl}-butyric acid methyl ester (87118-71-6) → (E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-8-(diisopropoxy-phosphoryl)-5-oxo-oct-6-enoic acid methyl ester (87118-72-7)

Guidance literature:

With water; pyridinium p-toluenesulfonate; In methanol; for 16h; Heating;

DOI:10.1016/S0040-4039(00)88094-6

Reference yield:

dimethyl 3-hydroxypentanedioate (7250-55-7) → (E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-8-(diisopropoxy-phosphoryl)-5-oxo-oct-6-enoic acid methyl ester (87118-72-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 80 percent / porcine liver esterase, Na₂HPO₄, H₂O / 12 h / Ambient temperature

2: 95 percent / imidazole, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

3: 80 percent / KOH, H₂O / 2-methyl-propan-2-ol / 2 h / 50 °C

4: 1.) carbonyldiimidazole / 1.) THF, rt, 3 h, 2.) rt, 12 h

6: 80 percent / Hg(OOCCF₃)2 / tetrahydrofuran / 24 h / Ambient temperature

7: 65 percent / BH₃-THF / tetrahydrofuran / 4 h / Ambient temperature

8: 85 percent / PCC, NaOAc / CH₂Cl₂ / 6 h / Ambient temperature

9: 99 percent / NaH / 0.08 h / Ambient temperature

10: 60 percent / H₂O, pyridinium p-toluenesulfonate / methanol / 16 h / Heating

With 1H-imidazole; porcine liver esterase; dmap; potassium hydroxide; disodium hydrogenphosphate; borane-THF; water; sodium acetate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; 1,1'-carbonyldiimidazole; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)88094-6

Reference yield:

(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[2-(2-oxo-ethyl)-[1,3]dioxolan-2-yl]-butyric acid methyl ester (87118-70-5) → (E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-8-(diisopropoxy-phosphoryl)-5-oxo-oct-6-enoic acid methyl ester (87118-72-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NaH / 0.08 h / Ambient temperature

2: 60 percent / H₂O, pyridinium p-toluenesulfonate / methanol / 16 h / Heating

With water; pyridinium p-toluenesulfonate; sodium hydride; In methanol;

DOI:10.1016/S0040-4039(00)88094-6

upstream raw materials:

(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{2-[(E)-3-(diisopropoxy-phosphoryl)-allyl]-[1,3]dioxolan-2-yl}-butyric acid methyl ester

dimethyl 3-hydroxypentanedioate

(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[2-(2-oxo-ethyl)-[1,3]dioxolan-2-yl]-butyric acid methyl ester

Monomethyl (3S)-(-)-3-hydroxypentanedioate

Downstream raw materials:

(6E,8E,10E,12E)-(S)-15-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-5-oxo-hexadeca-6,8,10,12-tetraenoic acid methyl ester