Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-hydroxy-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-deca-4,6,8-trienyl} ester

Base Information

• Chemical Name: Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-hydroxy-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-deca-4,6,8-trienyl} ester
• CAS No.: 1054611-67-4
• Molecular Formula: C₄₁H₅₉O₉PSi₂
• Molecular Weight: 783.059

Synonyms:Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-hydroxy-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-deca-4,6,8-trienyl} ester

Chemical Property of Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-hydroxy-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-deca-4,6,8-trienyl} ester

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Technology Process of Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-hydroxy-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-deca-4,6,8-trienyl} ester

There total 6 articles about Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-hydroxy-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-deca-4,6,8-trienyl} 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:

(R)-6-((E)-2-{(4R,5R)-2-Allyloxy-5-[(3Z,5Z,7E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-nona-3,5,7-trienyl]-4-methyl-2-oxo-2λ5-[1,3,2]dioxaphospholan-4-yl}-vinyl)-5,6-dihydro-pyran-2-one (1054645-76-9) → Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-hydroxy-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-deca-4,6,8-trienyl} ester (1054611-67-4)

Guidance literature:

(R)-6-((E)-2-{(4R,5R)-2-Allyloxy-5-[(3Z,5Z,7E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-nona-3,5,7-trienyl]-4-methyl-2-oxo-2λ⁵-[1,3,2]dioxaphospholan-4-yl}-vinyl)-5,6-dihydro-pyran-2-one; With 2,2,2-trifluoroethanol; triethylamine; at 20 ℃; for 1.5h;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium formate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 30h;

DOI:10.1021/ja030133v

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-hydroxy-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-deca-4,6,8-trienyl} ester (1054611-67-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

2.1: POCl₃; pyridine / 1 h / ice-cooling

3.1: pyridine / 0.5 h / ice-cooling

4.1: aq. 2,2,2-trifluoroethanol; triethylamine / 1.5 h / 20 °C

4.2: triphenylphosphine; HCO₂NH₄; Pd(PPh₃)4 / tetrahydrofuran / 30 h / 20 °C

With pyridine; 2,6-dimethylpyridine; 2,2,2-trifluoroethanol; triethylamine; trichlorophosphate; In dichloromethane;

DOI:10.1021/ja030133v

Reference yield:

(1Z,3E)-5-tert-butyldiphenylsilyloxy-1-tributylstannylpenta-1,3-diene → Phosphoric acid mono-{(4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-hydroxy-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-deca-4,6,8-trienyl} ester (1054611-67-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 52 percent / (MeCN)2PdCl₂ / 17.5 h / 20 °C

2.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

3.1: POCl₃; pyridine / 1 h / ice-cooling

4.1: pyridine / 0.5 h / ice-cooling

5.1: aq. 2,2,2-trifluoroethanol; triethylamine / 1.5 h / 20 °C

5.2: triphenylphosphine; HCO₂NH₄; Pd(PPh₃)4 / tetrahydrofuran / 30 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dichloro bis(acetonitrile) palladium(II); 2,2,2-trifluoroethanol; triethylamine; trichlorophosphate; In dichloromethane; 1.1: Stille coupling;

DOI:10.1021/ja030133v

upstream raw materials:

(R)-6-((E)-2-{(4R,5R)-2-Allyloxy-5-[(3Z,5Z,7E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-nona-3,5,7-trienyl]-4-methyl-2-oxo-2λ⁵-[1,3,2]dioxaphospholan-4-yl}-vinyl)-5,6-dihydro-pyran-2-one

t-butyldimethylsiyl triflate

(6R,1'E,3'R,4'R,6'R,7'Z,9'Z,11'E)-6-(6'-tert-butyldimethylsiloxy-13'-tert-butyldiphenylsiloxy-3',4'-dihydroxy-3'-methyl-1',7',9',11'-tridecatetraenyl)-5,6-dihydro-2H-pyran-2-one

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