(3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyric acid methyl ester

Base Information

Chemical Name:(3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyric acid methyl ester
CAS No.:915158-77-9
Molecular Formula:C₂₂H₃₆O₅Si
Molecular Weight:408.61
Hs Code.:

Synonyms:(3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyric acid methyl ester

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Chemical Property of (3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyric acid methyl ester

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Technology Process of (3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyric acid methyl ester

There total 8 articles about (3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyric acid methyl ester 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: 87.0%

: 915158-60-0
(R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-but-2-enoic acid methyl ester

: 917-54-4
methyllithium

: 915158-77-9
(3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyric acid methyl ester

: (3S,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyric acid methyl ester

Guidance literature:: With copper(l) iodide; chloro-trimethyl-silane; lithium bromide; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1021/ol0621710

Reference yield:

: 915158-58-6
(S)-(4-allyloxy-3-methoxyphenyl)-hydroxyacetonitrile

: 915158-77-9
(3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyric acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: HCl / diethyl ether / 5 - 15 °C

2: 10.4 g / H₂O / 0.5 h

3: 96 percent / imidazole / dimethylformamide / 0 - 20 °C

4: Dibal-H / toluene / 1.5 h / -78 °C

5: 2.73 g / CH₂Cl₂ / 12 h / 20 °C

6: 87 percent / LiBr; CuI; TMSCl / tetrahydrofuran / 3 h / -78 °C

With 1H-imidazole; hydrogenchloride; copper(l) iodide; chloro-trimethyl-silane; water; diisobutylaluminium hydride; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Wittig reaction;
DOI:10.1021/ol0621710

Reference yield:

: 915158-76-8
(S)-(4-allyloxy-3-methoxyphenyl)-hydroxy-acetic acid methyl ester

: 915158-77-9
(3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyric acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / imidazole / dimethylformamide / 0 - 20 °C

2: Dibal-H / toluene / 1.5 h / -78 °C

3: 2.73 g / CH₂Cl₂ / 12 h / 20 °C

4: 87 percent / LiBr; CuI; TMSCl / tetrahydrofuran / 3 h / -78 °C

With 1H-imidazole; copper(l) iodide; chloro-trimethyl-silane; diisobutylaluminium hydride; lithium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Wittig reaction;
DOI:10.1021/ol0621710