(E)-(2S,3R)-methyl 3-(dimethylphenylsilyl)-3-methyl-2-(trimethyulsilyloxy)-hex-4-enoate

Base Information

Chemical Name:(E)-(2S,3R)-methyl 3-(dimethylphenylsilyl)-3-methyl-2-(trimethyulsilyloxy)-hex-4-enoate
CAS No.:851759-74-5
Molecular Formula:C₁₉H₃₂O₃Si₂
Molecular Weight:364.632
Hs Code.:

Synonyms:(E)-(2S,3R)-methyl 3-(dimethylphenylsilyl)-3-methyl-2-(trimethyulsilyloxy)-hex-4-enoate

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Chemical Property of (E)-(2S,3R)-methyl 3-(dimethylphenylsilyl)-3-methyl-2-(trimethyulsilyloxy)-hex-4-enoate

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Technology Process of (E)-(2S,3R)-methyl 3-(dimethylphenylsilyl)-3-methyl-2-(trimethyulsilyloxy)-hex-4-enoate

There total 6 articles about (E)-(2S,3R)-methyl 3-(dimethylphenylsilyl)-3-methyl-2-(trimethyulsilyloxy)-hex-4-enoate 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: 97.0%

: 851760-06-0
(E)-(2S,3R)-methyl 2-hydroxy-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 851759-74-5
(E)-(2S,3R)-methyl 3-(dimethylphenylsilyl)-3-methyl-2-(trimethyulsilyloxy)-hex-4-enoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ol0501875

Reference yield:

: 851759-94-9
(Z)-(R)-4-(dimethyl-phenyl-silanyl)-pent-3-en-2-ol

: 851759-74-5
(E)-(2S,3R)-methyl 3-(dimethylphenylsilyl)-3-methyl-2-(trimethyulsilyloxy)-hex-4-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: TMSCl / tetrahydrofuran / -78 - 20 °C

3.1: 88 percent / NaHCO₃; Adogen-464(R) / CH₂Cl₂ / 20 °C

4.1: 72 percent / DDQ / CH₂Cl₂; H₂O / 0 - 20 °C

5.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

With 2,6-dimethylpyridine; dmap; Adogen-464(R); sodium hydrogencarbonate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol0501875

Reference yield:

: 851760-04-8
(Z)-(R)-(3-iodo-1-methyl-but-2-enyloxy)-dimethyl-phenyl-silane

: 851759-74-5
(E)-(2S,3R)-methyl 3-(dimethylphenylsilyl)-3-methyl-2-(trimethyulsilyloxy)-hex-4-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / t-BuLi / tetrahydrofuran / 2 h / -78 °C

2.1: 80 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

3.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: TMSCl / tetrahydrofuran / -78 - 20 °C

4.1: 88 percent / NaHCO₃; Adogen-464(R) / CH₂Cl₂ / 20 °C

5.1: 72 percent / DDQ / CH₂Cl₂; H₂O / 0 - 20 °C

6.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

With 2,6-dimethylpyridine; dmap; Adogen-464(R); tert.-butyl lithium; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol0501875