(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyraldehyde

Base Information

Chemical Name:(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyraldehyde
CAS No.:915158-62-2
Molecular Formula:C₂₂H₃₆O₄Si
Molecular Weight:392.611
Hs Code.:

Synonyms:(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyraldehyde

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Chemical Property of (2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyraldehyde

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Technology Process of (2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyraldehyde

There total 11 articles about (2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyraldehyde 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: 90.0%

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

: 915158-62-2
(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyraldehyde

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol0621710

Reference yield:

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

: 915158-62-2
(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyraldehyde

Guidance literature:: Multi-step reaction with 9 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

9: 90 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; copper(l) iodide; chloro-trimethyl-silane; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Wittig reaction / 9: Dess-Martin oxidation;
DOI:10.1021/ol0621710

Reference yield:

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

: 915158-62-2
(2R,3R,4R)-4-(4-allyloxy-3-methoxyphenyl)-4-(tert-butyldimethylsilanyloxy)-2,3-dimethylbutyraldehyde

Guidance literature:: Multi-step reaction with 7 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

7: 90 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; copper(l) iodide; chloro-trimethyl-silane; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; lithium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Wittig reaction / 7: Dess-Martin oxidation;
DOI:10.1021/ol0621710