Phosphorous acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester

Base Information

• Chemical Name: Phosphorous acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester
• CAS No.: 445235-79-0
• Molecular Formula: C₆₃H₈₉O₁₀PSi₃
• Molecular Weight: 1121.62

Synonyms:Phosphorous acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester

Chemical Property of Phosphorous acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester

Chemical Property:

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Technology Process of Phosphorous acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester

There total 8 articles about Phosphorous acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) 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:

t-butyldimethylsiyl triflate (69739-34-0) → Phosphorous acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester (445235-79-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 °C

2: 11 mg / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

3: 70 percent / aq. HCl / acetonitrile; tetrahydrofuran / 1.5 h / -10 °C

4: 84 percent / (MeCN)2PdCl₂ / dimethylformamide / 25 h / 20 °C

5: PCl₃; pyridine / 0.25 h / 0 °C

6: pyridine / 1 h / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dichloro bis(acetonitrile) palladium(II); phosphorus trichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4: Stille coupling;

DOI:10.1021/ja030133v

Reference yield:

(1Z,3E)-5-tert-butyldiphenylsilyloxy-1-tributylstannylpenta-1,3-diene → Phosphorous acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester (445235-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / (MeCN)2PdCl₂ / dimethylformamide / 25 h / 20 °C

2: PCl₃; pyridine / 0.25 h / 0 °C

3: pyridine / 1 h / 0 - 20 °C

With pyridine; dichloro bis(acetonitrile) palladium(II); phosphorus trichloride; In N,N-dimethyl-formamide; 1: Stille coupling;

DOI:10.1021/ja030133v

Reference yield:

(6R)-6-[(1E,3R,4R,6R,7Z)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-8-iodo-3-methyl-3-[(triethylsilyl)oxy]octa-1,7-dien-1-yl]-5,6-dihydro-2H-pyran-2-one (381665-44-7) → Phosphorous acid (4Z,6Z,8E)-(1R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-(R)-1-methyl-3-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-triethylsilanyloxy-allyl]-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester (445235-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / (MeCN)2PdCl₂ / dimethylformamide / 25 h / 20 °C

2: PCl₃; pyridine / 0.25 h / 0 °C

3: pyridine / 1 h / 0 - 20 °C

With pyridine; dichloro bis(acetonitrile) palladium(II); phosphorus trichloride; In N,N-dimethyl-formamide; 1: Stille coupling;

DOI:10.1021/ja030133v

upstream raw materials:

4-Methoxybenzyl alcohol

t-butyldimethylsiyl triflate

(6R)-6-[(1E,3R,4R,6R,7Z)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-8-iodo-3-methyl-3-[(triethylsilyl)oxy]octa-1,7-dien-1-yl]-5,6-dihydro-2H-pyran-2-one

(6R)-6-{(1E,3R,4R,6R,7Z,9Z,11E)-6-{[tert-butyl(dimethyl)silyl]oxy}-13-{[tert-butyl(diphenyl)silyl]oxy}-4-hydroxy-3-methyl-3-[(triethylsilyl)oxy]trideca-1,7,9,11-tetraen-1-yl}-5,6-dihydro-2H-pyran-2-one

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