(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutan-1-ol

Base Information

Chemical Name:(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutan-1-ol
CAS No.:915158-85-9
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

Synonyms:(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutan-1-ol

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Chemical Property of (2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutan-1-ol

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Technology Process of (2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutan-1-ol

There total 10 articles about (2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutan-1-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: 86.0%

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

: 915158-85-9
(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutan-1-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 - 0 ℃;
DOI:10.1021/ol0621710

Reference yield:

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

: 915158-85-9
(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutan-1-ol

Guidance literature:: Multi-step reaction with 8 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

8: 86 percent / Dibal-H / toluene / -78 - 0 °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

: 915158-85-9
(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutan-1-ol

Guidance literature:: Multi-step reaction with 6 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

6: 86 percent / Dibal-H / toluene / -78 - 0 °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