(1E,3E,5R,7R,8S)-9-(3,4-dimethoxybenzyloxy)-1-iodo-7-methoxy-8-methylnona-1,3-dien-5-yl propionate

Base Information

Chemical Name:(1E,3E,5R,7R,8S)-9-(3,4-dimethoxybenzyloxy)-1-iodo-7-methoxy-8-methylnona-1,3-dien-5-yl propionate
CAS No.:1256633-74-5
Molecular Formula:C₂₃H₃₃IO₆
Molecular Weight:532.416
Hs Code.:

Synonyms:(1E,3E,5R,7R,8S)-9-(3,4-dimethoxybenzyloxy)-1-iodo-7-methoxy-8-methylnona-1,3-dien-5-yl propionate

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Chemical Property of (1E,3E,5R,7R,8S)-9-(3,4-dimethoxybenzyloxy)-1-iodo-7-methoxy-8-methylnona-1,3-dien-5-yl propionate

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Technology Process of (1E,3E,5R,7R,8S)-9-(3,4-dimethoxybenzyloxy)-1-iodo-7-methoxy-8-methylnona-1,3-dien-5-yl propionate

There total 4 articles about (1E,3E,5R,7R,8S)-9-(3,4-dimethoxybenzyloxy)-1-iodo-7-methoxy-8-methylnona-1,3-dien-5-yl propionate 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: 89.0%

: trimethyloxonium tetrafluoroborate

: 1256633-60-9
C₂₂H₃₁IO₆

: 1256633-74-5
(1E,3E,5R,7R,8S)-9-(3,4-dimethoxybenzyloxy)-1-iodo-7-methoxy-8-methylnona-1,3-dien-5-yl propionate

Guidance literature:: In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol102425n

Reference yield:

: 1256633-59-6
(2S,5R,6E,8E)-1-(3,4-dimethoxybenzyloxy)-5-hydroxy-9-iodo-2-methylnona-6,8-dien-3-one

: 1256633-74-5
(1E,3E,5R,7R,8S)-9-(3,4-dimethoxybenzyloxy)-1-iodo-7-methoxy-8-methylnona-1,3-dien-5-yl propionate

Guidance literature:: Multi-step reaction with 2 steps

1: samarium diiodide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere

2: dichloromethane / 1 h / 20 °C / Inert atmosphere

With samarium diiodide; In tetrahydrofuran; dichloromethane; 1: Evans-Tishchenko reduction;
DOI:10.1021/ol102425n

Reference yield:

: 1256633-53-0
C₁₄H₂₀O₄

: 1256633-74-5
(1E,3E,5R,7R,8S)-9-(3,4-dimethoxybenzyloxy)-1-iodo-7-methoxy-8-methylnona-1,3-dien-5-yl propionate

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine; (-)-diisopinocamphenylborane chloride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere

1.2: 16.5 h / -78 - -20 °C / Inert atmosphere

2.1: samarium diiodide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere

3.1: dichloromethane / 1 h / 20 °C / Inert atmosphere

With samarium diiodide; triethylamine; (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Evans-Tishchenko reduction;
DOI:10.1021/ol102425n