(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyric acid methyl ester

Base Information

Chemical Name:(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyric acid methyl ester
CAS No.:915158-61-1
Molecular Formula:C₂₃H₃₈O₅Si
Molecular Weight:422.637
Hs Code.:

Synonyms:(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyric acid methyl ester

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Chemical Property of (2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyric acid methyl ester

Chemical Property:

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Technology Process of (2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyric acid methyl ester

There total 8 articles about (2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyric 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: 85.0%

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

: 74-88-4
methyl iodide

: (2S,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyric acid methyl ester

: 915158-61-1
(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyric acid methyl ester

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1021/ol0621710

Reference yield:

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

: 915158-61-1
(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyric acid methyl ester

Guidance literature:: Multi-step reaction with 7 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

7: 85 percent / NaHMDS / tetrahydrofuran / 3 h / -78 °C

With 1H-imidazole; hydrogenchloride; copper(l) iodide; chloro-trimethyl-silane; water; sodium hexamethyldisilazane; 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

: 915158-61-1
(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyric acid methyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 85 percent / NaHMDS / tetrahydrofuran / 3 h / -78 °C

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