ethyl (E)(S)-3-benzyloxymethyl-6-tert-butyldimethylsilanyloxy-3-methylhex-4-enate

Base Information

Chemical Name:ethyl (E)(S)-3-benzyloxymethyl-6-tert-butyldimethylsilanyloxy-3-methylhex-4-enate
CAS No.:220569-95-9
Molecular Formula:C₂₃H₃₈O₄Si
Molecular Weight:406.638
Hs Code.:

Synonyms:ethyl (E)(S)-3-benzyloxymethyl-6-tert-butyldimethylsilanyloxy-3-methylhex-4-enate

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Chemical Property of ethyl (E)(S)-3-benzyloxymethyl-6-tert-butyldimethylsilanyloxy-3-methylhex-4-enate

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Technology Process of ethyl (E)(S)-3-benzyloxymethyl-6-tert-butyldimethylsilanyloxy-3-methylhex-4-enate

There total 5 articles about ethyl (E)(S)-3-benzyloxymethyl-6-tert-butyldimethylsilanyloxy-3-methylhex-4-enate 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: 65.4%

: 78-39-7
Triethyl orthoacetate

: 220569-94-8
(E)(S)-5-benzyloxy-1-tert-butyldimethylsilanyloxy-4-methylpent-3-en-2-ol

: 220569-95-9
ethyl (E)(S)-3-benzyloxymethyl-6-tert-butyldimethylsilanyloxy-3-methylhex-4-enate

Guidance literature:: With propionic acid; at 135 ℃;
DOI:10.1016/S0040-4039(98)02324-7

Reference yield:

: 81997-76-4
(S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester

: 220569-95-9
ethyl (E)(S)-3-benzyloxymethyl-6-tert-butyldimethylsilanyloxy-3-methylhex-4-enate

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

2: 99 percent / sodium hydride / tetrahydrofuran / 3 h / 20 °C

3: 85 percent / 2N HCl / dioxane / 2 h / 20 °C

4: 92 percent / imidazole / CH₂Cl₂ / -10 °C

5: 65.4 percent / propionic acid / 4 h / 135 °C

With 1H-imidazole; hydrogenchloride; sodium hydride; diisobutylaluminium hydride; propionic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1: Reduction / 2: Alkylation / 3: Ring cleavage / 4: Alkylation / 5: Johnson-Claisen rearrangement;
DOI:10.1016/S0008-6215(00)00005-7

Reference yield:

: 108404-41-7
(E)(S)-4-(3-hydroxy-2-methylpropenyl)-2,2-dimethyl[1,3]dioxolane

: 220569-95-9
ethyl (E)(S)-3-benzyloxymethyl-6-tert-butyldimethylsilanyloxy-3-methylhex-4-enate

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / sodium hydride / tetrahydrofuran / 3 h / 20 °C

2: 85 percent / 2N HCl / dioxane / 2 h / 20 °C

3: 92 percent / imidazole / CH₂Cl₂ / -10 °C

4: 65.4 percent / propionic acid / 4 h / 135 °C

With 1H-imidazole; hydrogenchloride; sodium hydride; propionic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1: Alkylation / 2: Ring cleavage / 3: Alkylation / 4: Johnson-Claisen rearrangement;
DOI:10.1016/S0008-6215(00)00005-7