(3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(4-methoxybenzyl)oxy]methyl}hept-4-enal

Base Information

Chemical Name:(3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(4-methoxybenzyl)oxy]methyl}hept-4-enal
CAS No.:912654-39-8
Molecular Formula:C₂₂H₃₆O₄Si
Molecular Weight:392.611
Hs Code.:

Synonyms:(3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(4-methoxybenzyl)oxy]methyl}hept-4-enal

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Chemical Property of (3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(4-methoxybenzyl)oxy]methyl}hept-4-enal

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Technology Process of (3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(4-methoxybenzyl)oxy]methyl}hept-4-enal

There total 9 articles about (3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(4-methoxybenzyl)oxy]methyl}hept-4-enal 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%

: 912654-38-7
(3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(4-methoxybenzyl)oxy]methyl}hept-4-en-1-ol

: 912654-39-8
(3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(4-methoxybenzyl)oxy]methyl}hept-4-enal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 3.5h;
DOI:10.1021/jo061104g

Reference yield:

: 912654-35-4
(2E)-2-{[(4-methoxybenzyl)oxy]methyl}pent-2-enal

: 912654-39-8
(3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(4-methoxybenzyl)oxy]methyl}hept-4-enal

Guidance literature:: Multi-step reaction with 4 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.08 h / 0 °C

1.2: iPr₂NEt / CH₂Cl₂ / 2 h / -78 °C

1.3: 70 percent / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 23 °C

3.1: 84 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

4.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo061104g

Reference yield:

: 912654-34-3
(2Z)-2-{[(4-methoxybenzyl)oxy]methyl}pent-2-en-1-ol

: 912654-39-8
(3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-{[(4-methoxybenzyl)oxy]methyl}hept-4-enal

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 20 °C

2.1: TiCl₄ / CH₂Cl₂ / 0.08 h / 0 °C

2.2: iPr₂NEt / CH₂Cl₂ / 2 h / -78 °C

2.3: 70 percent / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 23 °C

4.1: 84 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

5.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo061104g