1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

Base Information

Chemical Name:1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-ol
CAS No.:916757-63-6
Molecular Formula:C₂₁H₃₄O₄Si
Molecular Weight:378.584
Hs Code.:

1-(<i>tert</i>-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

Synonyms:1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

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Chemical Property of 1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

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Technology Process of 1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

There total 1 articles about 1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-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: 89.0%

: 4039-83-2
3-(4-methoxybenzyloxy)propyne

: 95337-97-6,110171-85-2,130659-83-5,95338-04-8
(R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane

: 916757-63-6
1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

Guidance literature:: 3-(4-methoxybenzyloxy)propyne; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

(R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 4h;
DOI:10.1002/anie.200601867

Reference yield: 96.0%

: 916757-63-6
1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 916757-64-7
1-[5,7-bis-(tert-butyl-dimethyl-silanyloxy)-hept-2-ynyloxymethyl]-4-methoxy-benzene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 6h;
DOI:10.1002/anie.200601867 DOI:10.1021/ja068053p

Reference yield:

: 916757-63-6
1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

: 916757-47-6
[5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hept-2-enyloxymethyl]-benzene

Guidance literature:: Multi-step reaction with 7 steps

1.1: 96 percent / imidazole / dimethylformamide / 6 h / 25 °C

2.1: 79 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; aq. phosphate buffer / 3 h / 25 °C / pH 7

3.1: Red-Al / tetrahydrofuran; toluene / 0.75 h / 25 °C

3.2: 66 percent / N-iodosuccinimide / tetrahydrofuran; toluene / 0.5 h / -78 °C

4.1: triethylamine / tetrahydrofuran / 2 h / 25 °C

5.1: Pd(bis-(diphenylphosphino)ferrocene)Cl₂ / tetrahydrofuran; toluene / 12 h / 65 °C

6.1: 19.2 g / K₂CO₃ / methanol / 4 h / 25 °C

7.1: 88 percent / NaH; n-Bu₄NI / tetrahydrofuran / 6 h / 25 °C

With 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Negishi coupling;
DOI:10.1021/ja068053p