(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol

Base Information

Chemical Name:(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol
CAS No.:172327-03-6
Molecular Formula:C₂₇H₄₀O₅Si
Molecular Weight:472.697
Hs Code.:

Synonyms:(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol

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Chemical Property of (2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol

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Technology Process of (2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol

There total 4 articles about (2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol 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: 91.0%

: tert-Butyl-[(2S,3S)-2-(4-methoxy-benzyloxymethoxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-enyloxy]-diphenyl-silane

: 172327-03-6
(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol

Guidance literature:: With pH 7 buffer (KH₂PO₄-K₂HPO₄); 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; In dichloromethane; for 3h; Ambient temperature;
DOI:10.1021/jo00129a029

Reference yield:

: 146512-59-6
(2S,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-hexen-3-ol

: 172327-03-6
(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / n-Bu₄NI, Et(i-Pr)2N / dimethylformamide / 1.) room temp., 1 h, 2.) 70 deg C, overnight

2: 91 percent / t-BuOH, pH 7 buffer (KH₂PO₄-K₂HPO₄), DDQ / CH₂Cl₂ / 3 h / Ambient temperature

With pH 7 buffer (KH₂PO₄-K₂HPO₄); tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00129a029

Reference yield:

: 155003-29-5
(S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-hexen-3-on

: 172327-03-6
(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) 4 Angstroem mol. sieves, MgBr₂*Et₂O, 2.) DIBALH / 1.) Et₂O, -78 deg C, 15 min, 2.) toluene, -78 deg C, 15 min

2: 87 percent / n-Bu₄NI, Et(i-Pr)2N / dimethylformamide / 1.) room temp., 1 h, 2.) 70 deg C, overnight

3: 91 percent / t-BuOH, pH 7 buffer (KH₂PO₄-K₂HPO₄), DDQ / CH₂Cl₂ / 3 h / Ambient temperature

With 4 A molecular sieve; pH 7 buffer (KH₂PO₄-K₂HPO₄); tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; tert-butyl alcohol; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00129a029