{(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester

Base Information

Chemical Name:{(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester
CAS No.:712280-94-9
Molecular Formula:C₃₀H₄₀O₆Si
Molecular Weight:524.73
Hs Code.:

Synonyms:{(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester

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Chemical Property of {(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester

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Technology Process of {(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester

There total 6 articles about {(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester 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: 71.0%

: 78-39-7
Triethyl orthoacetate

: 712280-93-8
(1R,4S,6R)-4-benzyloxy-6-(tert-butyldimethylsilyloxy)-3-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol

: 712280-94-9
{(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester

Guidance literature:: With 4 A molecular sieve; 2-hydroxynitrobenzene; at 130 ℃; for 24h;
DOI:10.1016/j.tet.2007.05.041

Reference yield:

: 17680-04-5
(3,4-methylenedioxy)phenylmagnesium bromide

: 712280-94-9
{(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / tetrahydrofuran / 1 h / -100 °C

2: pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

3: 1.87 g / CeCl₃*7H₂O; NaBH₄ / methanol; CH₂Cl₂ / 0.5 h / -78 °C

4: 71 percent / 2-nitrophenol; molecular sieves 4 Angstroem / 24 h / 130 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; pyridinium chlorochromate; 2-hydroxynitrobenzene; In tetrahydrofuran; methanol; dichloromethane; 3: Luche reduction / 4: Johnson-Claisen rearrangement;
DOI:10.1016/j.tet.2007.05.041

Reference yield:

: 712280-92-7
(4S,6R)-4-benzyloxy-6-(tert-butyldimethylsilyloxy)-3-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-one

: 712280-94-9
{(1S,4R,6S)-1-[3',4'-(methylenedioxy)phenyl]-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexenyl}acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.87 g / CeCl₃*7H₂O; NaBH₄ / methanol; CH₂Cl₂ / 0.5 h / -78 °C

2: 71 percent / 2-nitrophenol; molecular sieves 4 Angstroem / 24 h / 130 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; 2-hydroxynitrobenzene; In methanol; dichloromethane; 1: Luche reduction / 2: Johnson-Claisen rearrangement;
DOI:10.1016/j.tet.2007.05.041