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

Base Information

• Chemical Name: (6Z,8E)-(2R,4S,R_S)-2,4-dihydroxy-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-6,8-decadienyl p-tolyl sulfoxide
• CAS No.: 405297-46-3
• Molecular Formula: C₂₃H₃₈O₄SSi
• Molecular Weight: 438.704

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

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

Chemical Property:

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

There total 6 articles about (6Z,8E)-(2R,4S,R_S)-2,4-dihydroxy-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-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: 84.0%

(1Z,3E)-5-[(1,1-dimethylethyl)dimethylsilyl]oxy-1,3-pentadienyl butyl telluride (185841-12-7) + (2R,4R,RS)-4,5-epoxy-2-hydroxypentyl p-tolyl sulfoxide (405297-45-2) → (6Z,8E)-(2R,4S,RS)-2,4-dihydroxy-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-6,8-decadienyl p-tolyl sulfoxide (405297-46-3)

Guidance literature:

(1Z,3E)-5-[(1,1-dimethylethyl)dimethylsilyl]oxy-1,3-pentadienyl butyl telluride; With BuCu(CN)(2-Th)Li₂; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

(2R,4R,R_S)-4,5-epoxy-2-hydroxypentyl p-tolyl sulfoxide; In tetrahydrofuran; hexane; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ja017177t

Reference yield:

(E)-2-penten-4-yn-1-ol (35042-52-5) → (6Z,8E)-(2R,4S,RS)-2,4-dihydroxy-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-6,8-decadienyl p-tolyl sulfoxide (405297-46-3)

Guidance literature:

Multi-step reaction with 3 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

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

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)-2,4-dihydroxy-10-[(1,1-dimethylethyl)dimethylsilyl]oxy-6,8-decadienyl p-tolyl sulfoxide (405297-46-3)

Guidance literature:

Multi-step reaction with 2 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

With sodium tetrahydroborate; BuCu(CN)(2-Th)Li₂; In tetrahydrofuran; ethanol; hexane;

DOI:10.1021/ja017177t

upstream raw materials:

(1Z,3E)-5-[(1,1-dimethylethyl)dimethylsilyl]oxy-1,3-pentadienyl butyl telluride

(2R,4R,R_S)-4,5-epoxy-2-hydroxypentyl p-tolyl sulfoxide

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

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

Downstream raw materials:

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

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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