(4S,5S)-4-(tert-butyldimethyl)silyloxy-5-(4-methoxybenzyloxy)-1-hexanol

Base Information

Chemical Name:(4S,5S)-4-(tert-butyldimethyl)silyloxy-5-(4-methoxybenzyloxy)-1-hexanol
CAS No.:370094-53-4
Molecular Formula:C₂₀H₃₆O₄Si
Molecular Weight:368.589
Hs Code.:

Synonyms:(4S,5S)-4-(tert-butyldimethyl)silyloxy-5-(4-methoxybenzyloxy)-1-hexanol

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Chemical Property of (4S,5S)-4-(tert-butyldimethyl)silyloxy-5-(4-methoxybenzyloxy)-1-hexanol

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Technology Process of (4S,5S)-4-(tert-butyldimethyl)silyloxy-5-(4-methoxybenzyloxy)-1-hexanol

There total 6 articles about (4S,5S)-4-(tert-butyldimethyl)silyloxy-5-(4-methoxybenzyloxy)-1-hexanol 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: 88.0%

: 263761-20-2
tert-butyl(((2S,3S)-2-((4-methoxybenzyl)oxy)-hex-5-en-3-yl)oxy)dimethylsilane

: 370094-53-4
(4S,5S)-4-(tert-butyldimethyl)silyloxy-5-(4-methoxybenzyloxy)-1-hexanol

Guidance literature:: tert-butyl(((2S,3S)-2-((4-methoxybenzyl)oxy)-hex-5-en-3-yl)oxy)dimethylsilane; With Wilkinson's catalyst; benzo[1,3,2]dioxaborole; In tetrahydrofuran; for 1.16667h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; ethanol; for 0.25h; Further stages.;
DOI:10.1021/jo015756a

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 370094-53-4
(4S,5S)-4-(tert-butyldimethyl)silyloxy-5-(4-methoxybenzyloxy)-1-hexanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 82 percent / CF₃SO₃H / cyclohexane; CH₂Cl₂ / 0.75 h

2.1: DIBAL / various solvent(s); CH₂Cl₂ / 2.25 h / -78 °C

3.1: 84 percent / MgBr₂*OEt₂ / CH₂Cl₂ / -23 °C

4.1: 53.4 g / imidazole / dimethylformamide / 12.5 h / 23 °C

5.1: catecholborane; (Ph₃P)3RhCl / tetrahydrofuran / 1.17 h

5.2: 88 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; ethanol / 0.25 h

With 1H-imidazole; Wilkinson's catalyst; trifluorormethanesulfonic acid; diisobutylaluminium hydride; magnesium bromide; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1021/jo015756a

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 370094-53-4
(4S,5S)-4-(tert-butyldimethyl)silyloxy-5-(4-methoxybenzyloxy)-1-hexanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 53.4 g / imidazole / dimethylformamide / 12.5 h / 23 °C

2.1: catecholborane; (Ph₃P)3RhCl / tetrahydrofuran / 1.17 h

2.2: 88 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; ethanol / 0.25 h

With 1H-imidazole; Wilkinson's catalyst; benzo[1,3,2]dioxaborole; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo015756a