(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene

Base Information

Chemical Name:(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene
CAS No.:184291-95-0
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

Synonyms:(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene

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Chemical Property of (2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene

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Technology Process of (2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene

There total 3 articles about (2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene 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: 93.0%

: 2746-25-0
p-Methoxybenzyl bromide

: 106296-58-6
(2S,3S,4S)-(1-tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-en-3-ol

: 184291-95-0
(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; for 48h; Ambient temperature;
DOI:10.1021/ja961374o

Reference yield:

: 105-13-5
4-Methoxybenzyl alcohol

: 184291-95-0
(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene

Guidance literature:: Multi-step reaction with 2 steps

1: 48percent aq. HBr / 0.5 h / Ambient temperature

2: 93 percent / NaH / dimethylformamide; tetrahydrofuran / 48 h / Ambient temperature

With hydrogen bromide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja961374o

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 184291-95-0
(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / imidazole / dimethylformamide

2.1: 97 percent / DIBAl / CH₂Cl₂ / -40 °C

3.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: molecular sieves 4 Angstroem / toluene / 0.33 h / 20 °C

4.2: 13.1 g / toluene / 3 h / -78 °C

5.1: 89 percent / NaH / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

With 1H-imidazole; oxalyl dichloride; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Swern oxidation;
DOI:10.1016/S0968-0896(03)00186-X