(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

Base Information

• Chemical Name: (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
• CAS No.: 1054645-76-9
• Molecular Formula: C₄₄H₆₁O₈PSi₂
• Molecular Weight: 805.108

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (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

There total 5 articles about (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 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) → (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)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

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

3: pyridine / 0.5 h / ice-cooling

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

DOI:10.1021/ja030133v

Reference yield:

(1Z,3E)-5-tert-butyldiphenylsilyloxy-1-tributylstannylpenta-1,3-diene → (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)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / (MeCN)2PdCl₂ / 17.5 h / 20 °C

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

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

4: pyridine / 0.5 h / ice-cooling

With pyridine; 2,6-dimethylpyridine; dichloro bis(acetonitrile) palladium(II); trichlorophosphate; In dichloromethane; 1: Stille coupling;

DOI:10.1021/ja030133v

Reference yield:

(6R,1'E/Z,3'R,4'R,6'R,7'E/Z)-6-(8'-iodo-3'-methyl-3',4',6-trihydroxy-1',7'-octadienyl)-5,6-dihydro-2H-pyran-2-one → (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)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / (MeCN)2PdCl₂ / 17.5 h / 20 °C

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

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

4: pyridine / 0.5 h / ice-cooling

With pyridine; 2,6-dimethylpyridine; dichloro bis(acetonitrile) palladium(II); trichlorophosphate; In dichloromethane; 1: Stille coupling;

DOI:10.1021/ja030133v

upstream raw materials:

allyl alcohol

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

Downstream raw materials:

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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