(2S,3S,4S,5R)-1-(4-dimethylphenylsilyl-5-hydroxymethyl-2,3,5-trimethyltetra-hydrofuran-3-yl)ethanone

Base Information

Chemical Name:(2S,3S,4S,5R)-1-(4-dimethylphenylsilyl-5-hydroxymethyl-2,3,5-trimethyltetra-hydrofuran-3-yl)ethanone
CAS No.:257627-70-6
Molecular Formula:C₁₈H₂₈O₃Si
Molecular Weight:320.504
Hs Code.:

Synonyms:(2S,3S,4S,5R)-1-(4-dimethylphenylsilyl-5-hydroxymethyl-2,3,5-trimethyltetra-hydrofuran-3-yl)ethanone

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Chemical Property of (2S,3S,4S,5R)-1-(4-dimethylphenylsilyl-5-hydroxymethyl-2,3,5-trimethyltetra-hydrofuran-3-yl)ethanone

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Technology Process of (2S,3S,4S,5R)-1-(4-dimethylphenylsilyl-5-hydroxymethyl-2,3,5-trimethyltetra-hydrofuran-3-yl)ethanone

There total 7 articles about (2S,3S,4S,5R)-1-(4-dimethylphenylsilyl-5-hydroxymethyl-2,3,5-trimethyltetra-hydrofuran-3-yl)ethanone 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: 84.0%

: 257627-69-3
(2S,3S,4S,5R)-1-[5-((tert-butyldiphenylsiloxy)methyl)-4-(dimethylphenylsilyl)-2,3,5-trimethyltetrahydrofuran-3-yl]ethanone

: 257627-70-6
(2S,3S,4S,5R)-1-(4-dimethylphenylsilyl-5-hydroxymethyl-2,3,5-trimethyltetra-hydrofuran-3-yl)ethanone

Guidance literature:: With pyridine; hydrogen fluoride; In water; acetonitrile; at 20 ℃; for 18h;
DOI:10.1021/ol991315q

Reference yield:

: 101150-39-4
E-1-iodo-1-(dimethylphenylsilyl)propene

: 257627-70-6
(2S,3S,4S,5R)-1-(4-dimethylphenylsilyl-5-hydroxymethyl-2,3,5-trimethyltetra-hydrofuran-3-yl)ethanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: TaCl₅; Zn / benzene; 1,2-dimethoxy-ethane / 3 h

1.2: tetrahydrofuran; benzene; 1,2-dimethoxy-ethane / 1 h

1.3: aq. NaOH / tetrahydrofuran; benzene; 1,2-dimethoxy-ethane / 2 h

2.1: 82 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

3.1: 99 percent / imidazole / CH₂Cl₂ / 0.17 h / 0 °C

4.1: 47 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / -30 °C

5.1: 84 percent / HF; C₅H₅N / acetonitrile; H₂O / 18 h / 20 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; tetrabutyl ammonium fluoride; tantalum pentachloride; zinc; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; acetonitrile; benzene; 1.1: Metallation / 1.2: Addition / 1.3: Hydrolysis / 2.1: Substitution / 3.1: Substitution / 4.1: Condensation / 5.1: Hydrolysis;
DOI:10.1021/ol991315q

Reference yield:

: 257627-65-9
(2S,3RS)-5-(dimethylphenylsilyl)-3,4-dimethyl-(E)-pent-4-ene-2,3-diol

: 257627-70-6
(2S,3S,4S,5R)-1-(4-dimethylphenylsilyl-5-hydroxymethyl-2,3,5-trimethyltetra-hydrofuran-3-yl)ethanone

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / imidazole / CH₂Cl₂ / 0.17 h / 0 °C

2: 47 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / -30 °C

3: 84 percent / HF; C₅H₅N / acetonitrile; H₂O / 18 h / 20 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; In dichloromethane; water; acetonitrile; 1: Substitution / 2: Condensation / 3: Hydrolysis;
DOI:10.1021/ol991315q