(6Z,8E)-(2R,4S,R_S)-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-2,4-isopropylidenedioxy-6,8-decadienyl p-tolyl sulfoxide

Base Information

• Chemical Name: (6Z,8E)-(2R,4S,R_S)-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-2,4-isopropylidenedioxy-6,8-decadienyl p-tolyl sulfoxide
• CAS No.: 405297-47-4
• Molecular Formula: C₂₆H₄₂O₄SSi
• Molecular Weight: 478.769

Synonyms:(6Z,8E)-(2R,4S,R_S)-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-2,4-isopropylidenedioxy-6,8-decadienyl p-tolyl sulfoxide

Chemical Property of (6Z,8E)-(2R,4S,R_S)-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-2,4-isopropylidenedioxy-6,8-decadienyl p-tolyl sulfoxide

Chemical Property:

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Technology Process of (6Z,8E)-(2R,4S,R_S)-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-2,4-isopropylidenedioxy-6,8-decadienyl p-tolyl sulfoxide

There total 8 articles about (6Z,8E)-(2R,4S,R_S)-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-2,4-isopropylidenedioxy-6,8-decadienyl p-tolyl sulfoxide 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: 88.0%

2,2-dimethoxy-propane (77-76-9) + (6Z,8E)-(2R,4S,RS)-2,4-dihydroxy-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-6,8-decadienyl p-tolyl sulfoxide (405297-46-3) → (6Z,8E)-(2R,4S,RS)-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-2,4-isopropylidenedioxy-6,8-decadienyl p-tolyl sulfoxide (405297-47-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; acetone; at 20 ℃; for 5h;

DOI:10.1021/ja017177t

Reference yield:

(E)-2-penten-4-yn-1-ol (35042-52-5) → (6Z,8E)-(2R,4S,RS)-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-2,4-isopropylidenedioxy-6,8-decadienyl p-tolyl sulfoxide (405297-47-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / imidazole / tetrahydrofuran; dimethylformamide / 12 h / 20 °C

2.1: 92 percent / NaBH₄ / ethanol / 5.5 h / Heating

3.1: BuCu(CN)(2-Th)Li₂ / tetrahydrofuran; hexane / 1 h / 20 °C

3.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C

4.1: 88 percent / PPTS / CH₂Cl₂; acetone / 5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; BuCu(CN)(2-Th)Li₂; pyridinium p-toluenesulfonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja017177t

Reference yield:

(E)-5-[(1,1-dimethylethyl)dimethylsilyl]oxypent-3-en-1-yne (88832-56-8,128551-05-3,117970-56-6) → (6Z,8E)-(2R,4S,RS)-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-2,4-isopropylidenedioxy-6,8-decadienyl p-tolyl sulfoxide (405297-47-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / NaBH₄ / ethanol / 5.5 h / Heating

2.1: BuCu(CN)(2-Th)Li₂ / tetrahydrofuran; hexane / 1 h / 20 °C

2.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 88 percent / PPTS / CH₂Cl₂; acetone / 5 h / 20 °C

With sodium tetrahydroborate; BuCu(CN)(2-Th)Li₂; pyridinium p-toluenesulfonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetone;

DOI:10.1021/ja017177t

upstream raw materials:

2,2-dimethoxy-propane

(6Z,8E)-(2R,4S,R_S)-2,4-dihydroxy-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-6,8-decadienyl p-tolyl sulfoxide

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

(E)-5-[(1,1-dimethylethyl)dimethylsilyl]oxypent-3-en-1-yne

Downstream raw materials:

Benzoic acid (R)-2-benzenesulfonyl-1-((E)-2-{(4R,6S)-6-[(2Z,4E)-6-(tert-butyl-dimethyl-silanyloxy)-hexa-2,4-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-vinyl)-6-triisopropylsilanyloxy-heptyl ester

(2E,4Z,10E,12E)-(7S,9R,17R)-1-[(1,1-dimethylethyl)silyl]oxy-7,9-isopropylidenedioxy-12-(phenylsulfonyl)-17-[tris(1-methylethyl)silyl]oxyoctadeca-2,4,10,12-tetraene

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