N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

Base Information

Chemical Name:N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol
CAS No.:882048-66-0
Molecular Formula:C₃₂H₄₉NO₄Si
Molecular Weight:539.831
Hs Code.:

Synonyms:N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

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Chemical Property of N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

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Technology Process of N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

There total 7 articles about N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol 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: 90.0%

: 882048-85-3
N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-N-trifluoroacetyl-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

: 882048-66-0
N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃;
DOI:10.1021/ol060019s

Reference yield:

: 882048-19-3
(E)-3-(3'-tert-butyldimethylsilyloxy)-benzyl-4-O-(tetrahydro-2'H-pyran-2'-yl)-2-buten-1,4-diol

: 882048-66-0
N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / n-butyllithium / tetrahydrofuran / 5.5 h / -78 °C

2: 83 percent / PdCl₂(CH₃CN)2 / benzene / 13.5 h / 20 °C

3: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

4: 100 percent / 4-dimethylaminopyridine; imidazole / CH₂Cl₂ / 10 h / 20 °C

5: 90 percent / sodium borohydride / ethanol / 0 - 20 °C

With 1H-imidazole; dmap; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; ethanol; dichloromethane; benzene;
DOI:10.1021/ol060019s

Reference yield:

: (Z)-3-tributylstannyl-4-tetrahydro-2'H-pyran-2'-yl-2-buten-1,4-diol

: 882048-66-0
N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / triphenylarsine; Pd₂dba3 / tetrahydrofuran / 6 h / Heating

2: 95 percent / n-butyllithium / tetrahydrofuran / 5.5 h / -78 °C

3: 83 percent / PdCl₂(CH₃CN)2 / benzene / 13.5 h / 20 °C

4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5: 100 percent / 4-dimethylaminopyridine; imidazole / CH₂Cl₂ / 10 h / 20 °C

6: 90 percent / sodium borohydride / ethanol / 0 - 20 °C

With 1H-imidazole; dmap; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; triphenyl-arsane; tetrabutyl ammonium fluoride; In tetrahydrofuran; ethanol; dichloromethane; benzene; 1: Stille coupling;
DOI:10.1021/ol060019s