(E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-ol

Base Information

Chemical Name:(E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-ol
CAS No.:861902-90-1
Molecular Formula:C₁₉H₂₆O₆
Molecular Weight:350.412
Hs Code.:

Synonyms:(E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-ol

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Chemical Property of (E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-ol

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Technology Process of (E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-ol

There total 3 articles about (E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-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: 91.0%

: 861902-94-5
(S,E)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-one

: 861902-90-1
(E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-ol

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; dichloromethane; at -78 ℃; for 0.166667h;
DOI:10.1021/ol0508429

Reference yield:

: 861902-93-4
(S)-N-methoxy-2-((4-methoxybenzyl)oxy)-N-methylpropanamide

: 861902-90-1
(E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: t-BuLi / diethyl ether; pentane / 5 h / -40 °C

1.2: 90 percent / pentane; diethyl ether / 12 h / 20 °C

2.1: 91 percent / LiEt₃BH / tetrahydrofuran; CH₂Cl₂ / 0.17 h / -78 °C

With tert.-butyl lithium; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;
DOI:10.1021/ol0508429

Reference yield:

: 229647-61-4
(S)-2-((4-methoxybenzyl)oxy)propanoic acid

: 861902-90-1
(E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-methylmorpholine; pivaloyl chloride / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 90 percent / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: t-BuLi / diethyl ether; pentane / 5 h / -40 °C

2.2: 90 percent / pentane; diethyl ether / 12 h / 20 °C

3.1: 91 percent / LiEt₃BH / tetrahydrofuran; CH₂Cl₂ / 0.17 h / -78 °C

With 4-methyl-morpholine; tert.-butyl lithium; pivaloyl chloride; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;
DOI:10.1021/ol0508429