1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate

Base Information

• Chemical Name: 1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate
• CAS No.: 411242-10-9
• Molecular Formula: C₆₇H₁₀₁O₉PSi₅
• Molecular Weight: 1221.93
• Mol file: 411242-10-9.mol

Synonyms:1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate

Chemical Property of 1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate

There total 22 articles about 1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate 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:

tert-butylchlorodiphenylsilane (58479-61-1) → 1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate (411242-10-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 85 percent / imidazole / CH₂Cl₂ / 2 h / 0 °C

2.1: Cy₃P; Et₃N / [Rh(cod)Cl]2 / cyclohexane / 0.5 h / 23 °C

2.2: 74 percent / cyclohexane / 4 h / 23 °C

3.1: 74 percent / Ag₂O / Pd(PPh₃)4 / tetrahydrofuran / 8 h / 65 °C

4.1: 67 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

5.1: PCl₃; pyridine / 0.17 h / 0 °C

6.1: pyridine / 1 h / 0 - 23 °C

7.1: H₂O₂ / pyridine; CH₂Cl₂; H₂O / 1 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dihydrogen peroxide; triethylamine; silver(l) oxide; tricyclohexylphosphine; phosphorus trichloride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; dichloromethane; cyclohexane; water; 3.1: Suzuki-Miyaura cross-coupling;

DOI:10.1021/ol025537r

Reference yield:

Phosphorous acid (4Z,6Z,8E)-(1R,3R)-1-[(E)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-3,10-bis-(tert-butyl-diphenyl-silanyloxy)-deca-4,6,8-trienyl ester bis-(2-trimethylsilanyl-ethyl) ester → 1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate (411242-10-9)

Guidance literature:

With dihydrogen peroxide; In pyridine; dichloromethane; water; at 20 ℃; for 1h;

DOI:10.1021/ol025537r

Reference yield:

(E)-2-penten-4-yn-1-ol (35042-52-5) → 1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate (411242-10-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 85 percent / imidazole / CH₂Cl₂ / 2 h / 0 °C

2.1: Cy₃P; Et₃N / [Rh(cod)Cl]2 / cyclohexane / 0.5 h / 23 °C

2.2: 74 percent / cyclohexane / 4 h / 23 °C

3.1: 74 percent / Ag₂O / Pd(PPh₃)4 / tetrahydrofuran / 8 h / 65 °C

4.1: 67 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

5.1: PCl₃; pyridine / 0.17 h / 0 °C

6.1: pyridine / 1 h / 0 - 23 °C

7.1: H₂O₂ / pyridine; CH₂Cl₂; H₂O / 1 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dihydrogen peroxide; triethylamine; silver(l) oxide; tricyclohexylphosphine; phosphorus trichloride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; dichloromethane; cyclohexane; water; 3.1: Suzuki-Miyaura cross-coupling;

DOI:10.1021/ol025537r

upstream raw materials:

(E)-2-penten-4-yn-1-ol

tert-butylchlorodiphenylsilane

(E)-tert-butyl(pent-2-en-4-yn-1-yloxy)diphenylsilane

5-hexen-1-yn-3(R)-ol