4-Octadecen-3-ol, 2-azido-1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2S,3R,4E)-

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Chemical Name:4-Octadecen-3-ol, 2-azido-1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2S,3R,4E)-
CAS No.:916159-70-1
Molecular Formula:C34H53N3O2Si
Molecular Weight:563.899
Hs Code.:

Synonyms:

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Chemical Property of 4-Octadecen-3-ol, 2-azido-1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2S,3R,4E)-

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Technology Process of 4-Octadecen-3-ol, 2-azido-1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2S,3R,4E)-

There total 9 articles about 4-Octadecen-3-ol, 2-azido-1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2S,3R,4E)- 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: 87.0%

: 916159-69-8
[(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane

: 916159-70-1
(2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol

Guidance literature:: [(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane; With tetra-(n-butyl)ammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 2h; Heating;

With sulfuric acid; In tetrahydrofuran; water; toluene; at 20 ℃; for 1h;
DOI:10.1021/jo0614543

Reference yield:

: 916159-68-7
(2S,3S,4R)-2-azido-1-(tert-butyldiphenylsilyloxy)octadecane-3,4-diol

: 916159-70-1
(2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: thionyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl₄; acetonitrile; H₂O / 2 h / 20 °C

3.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating

3.2: 87 percent / sulfuric acid / toluene; tetrahydrofuran; H₂O / 1 h / 20 °C

With ruthenium trichloride; sodium periodate; thionyl chloride; tetra-(n-butyl)ammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrachloromethane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jo0614543

Reference yield:

: 554-62-1
D-ribo-phytosphingosine

: 916159-70-1
(2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: trifluoromethanesulfonyl azide; potassium carbonate; copper(II) sulfate / methanol; H₂O; CH₂Cl₂ / 3 h / 20 °C

2.1: 87 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂; dimethylformamide / 24 h / 20 °C

3.1: thionyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl₄; acetonitrile; H₂O / 2 h / 20 °C

5.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating

5.2: 87 percent / sulfuric acid / toluene; tetrahydrofuran; H₂O / 1 h / 20 °C

With dmap; ruthenium trichloride; sodium periodate; thionyl chloride; triflic azide; tetra-(n-butyl)ammonium iodide; potassium carbonate; copper(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo0614543