(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

Base Information

Chemical Name:(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al
CAS No.:251319-56-9
Molecular Formula:C₂₀H₃₂O₃Si
Molecular Weight:348.558
Hs Code.:

Synonyms:(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

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Chemical Property of (2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

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Technology Process of (2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

There total 9 articles about (2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al 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: 89.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 251319-55-8
(R)-4-Benzyl-3-((E)-(2R,3S)-6-benzyloxy-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one

: 251319-56-9
(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

Guidance literature:: (R)-4-Benzyl-3-((E)-(2R,3S)-6-benzyloxy-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one; With trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride; In tetrahydrofuran; at -15 ℃;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(99)01481-1

Reference yield:

: 321921-83-9
(E)-(2R,3S)-6-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hex-4-enoic acid methoxy-methyl-amide

: 251319-56-9
(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1016/S0040-4020(00)00804-8

Reference yield:

: 69152-87-0
4-benzyloxycrotonaldehyde

: 251319-56-9
(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

Guidance literature:: Multi-step reaction with 4 steps

1.1: dibutylboron triflate / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 100 percent / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.1: Al(CH₃)3 / tetrahydrofuran; toluene / 2.5 h / 0 °C

2.2: aq. HCl / CH₂Cl₂ / 18 h / 0 °C

3.1: 14.1 g / imidazole / dimethylformamide / 18 h

4.1: 10.7 g / DIBAL / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: deprotonation / 1.2: Addition / 2.1: Substitution / 2.2: Hydrolysis / 3.1: Substitution / 4.1: Reduction;
DOI:10.1016/S0040-4020(00)00804-8