(S,Z)-4-((4S,6S)-6-((R,Z)-4-(4-methoxybenzyloxy)-1-(triphenylstannyl)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-(triphenylstannyl)pent-2-en-1-ol

Base Information

• Chemical Name: (S,Z)-4-((4S,6S)-6-((R,Z)-4-(4-methoxybenzyloxy)-1-(triphenylstannyl)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-(triphenylstannyl)pent-2-en-1-ol
• CAS No.: 1554321-52-6
• Molecular Formula: C₆₆H₇₆O₅Sn₂
• Molecular Weight: 1186.75

Synonyms:(S,Z)-4-((4S,6S)-6-((R,Z)-4-(4-methoxybenzyloxy)-1-(triphenylstannyl)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-(triphenylstannyl)pent-2-en-1-ol

Chemical Property of (S,Z)-4-((4S,6S)-6-((R,Z)-4-(4-methoxybenzyloxy)-1-(triphenylstannyl)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-(triphenylstannyl)pent-2-en-1-ol

Chemical Property:

Purity/Quality:

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Technology Process of (S,Z)-4-((4S,6S)-6-((R,Z)-4-(4-methoxybenzyloxy)-1-(triphenylstannyl)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-(triphenylstannyl)pent-2-en-1-ol

There total 14 articles about (S,Z)-4-((4S,6S)-6-((R,Z)-4-(4-methoxybenzyloxy)-1-(triphenylstannyl)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-(triphenylstannyl)pent-2-en-1-ol 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%

(S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-yn-1-ol (1554321-50-4) + triphenylstannane (892-20-6) → (S,Z)-4-((4S,6S)-6-((R,Z)-4-(4-methoxybenzyloxy)-1-(triphenylstannyl)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-(triphenylstannyl)pent-2-en-1-ol (1554321-52-6)

Guidance literature:

(S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-yn-1-ol; triphenylstannane; With triethyl borane; In hexane; toluene; at 20 ℃; for 0.166667h; Inert atmosphere;

In hexane; toluene; at 20 ℃; for 14h;

DOI:10.1021/ol500050p

Reference yield:

(R)-2-hydroxyheptyl p-toluenesulfonate (80800-66-4,120925-79-3) → (S,Z)-4-((4S,6S)-6-((R,Z)-4-(4-methoxybenzyloxy)-1-(triphenylstannyl)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-(triphenylstannyl)pent-2-en-1-ol (1554321-52-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium hydride / diethyl ether; mineral oil / 43 h / 0 - 20 °C / Inert atmosphere

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 151 h / 0 - 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / dichloromethane / 143 h / 20 °C / Inert atmosphere

4.1: zinc trifluoromethanesulfonate; (-)-N-methylephedrine; triethylamine / tetrahydrofuran / 0.35 h / 20 °C / Inert atmosphere

4.2: 48 h / 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -78 - -30 °C

6.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C / Inert atmosphere

7.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane / 74 h / 20 °C

8.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

8.2: 37 h / -78 - -20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5.17 h / 0 - 20 °C

10.1: toluene-4-sulfonic acid / acetone / 13.5 h / 20 °C / Inert atmosphere

11.1: sodium; methanol / 19 h / 20 °C / Inert atmosphere

12.1: triethyl borane / toluene; hexane / 0.17 h / 20 °C / Inert atmosphere

12.2: air / 14 h / 20 °C

With 2,6-dimethylpyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; triethyl borane; [bis(acetoxy)iodo]benzene; (-)-N-methylephedrine; tetrabutyl ammonium fluoride; palladium diacetate; sodium; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone; toluene; mineral oil;

DOI:10.1021/ol500050p

Reference yield:

(R)-1,2-epoxyheptane (110549-07-0) → (S,Z)-4-((4S,6S)-6-((R,Z)-4-(4-methoxybenzyloxy)-1-(triphenylstannyl)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-(triphenylstannyl)pent-2-en-1-ol (1554321-52-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 151 h / 0 - 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / dichloromethane / 143 h / 20 °C / Inert atmosphere

3.1: zinc trifluoromethanesulfonate; (-)-N-methylephedrine; triethylamine / tetrahydrofuran / 0.35 h / 20 °C / Inert atmosphere

3.2: 48 h / 20 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -78 - -30 °C

5.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C / Inert atmosphere

6.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane / 74 h / 20 °C

7.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

7.2: 37 h / -78 - -20 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5.17 h / 0 - 20 °C

9.1: toluene-4-sulfonic acid / acetone / 13.5 h / 20 °C / Inert atmosphere

10.1: sodium; methanol / 19 h / 20 °C / Inert atmosphere

11.1: triethyl borane / toluene; hexane / 0.17 h / 20 °C / Inert atmosphere

11.2: air / 14 h / 20 °C

With 2,6-dimethylpyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; triethyl borane; [bis(acetoxy)iodo]benzene; (-)-N-methylephedrine; tetrabutyl ammonium fluoride; palladium diacetate; sodium; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene;

DOI:10.1021/ol500050p

upstream raw materials:

(R)-2-hydroxyheptyl p-toluenesulfonate

(R)-1,2-epoxyheptane

(R)-(+)-non-1-yn-4-ol

1-Heptene

Downstream raw materials:

C₇₂H₉₀O₅SiSn₂

tert-butyl((S,Z)-2-iodo-4-((4S,6S)-6-((R,Z)-1-iodo-4-(4-methoxybenzyloxy)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-enyloxy)dimethylsilane

tert-butyl((S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-enyloxy)dimethylsilane

(S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-en-1-ol

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