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

Base Information

Chemical Name:2-{(1'S,4'R,6'S)-1'-[3'',4''-(methylenedioxy)phenyl]-6'-benzyloxy-4'-(tert-butyldimethylsilyloxy)-2'-cyclohexenyl}ethanol
CAS No.:712280-95-0
Molecular Formula:C₂₈H₃₈O₅Si
Molecular Weight:482.692
Hs Code.:

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

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

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

There total 7 articles about 2-{(1'S,4'R,6'S)-1'-[3'',4''-(methylenedioxy)phenyl]-6'-benzyloxy-4'-(tert-butyldimethylsilyloxy)-2'-cyclohexenyl}ethanol 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: 97.0%

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

: 712280-95-0
2-{(1'S,4'R,6'S)-1'-[3'',4''-(methylenedioxy)phenyl]-6'-benzyloxy-4'-(tert-butyldimethylsilyloxy)-2'-cyclohexenyl}ethanol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at 0 ℃; for 0.666667h;
DOI:10.1039/b402762k

Reference yield:

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

: 712280-95-0
2-{(1'S,4'R,6'S)-1'-[3'',4''-(methylenedioxy)phenyl]-6'-benzyloxy-4'-(tert-butyldimethylsilyloxy)-2'-cyclohexenyl}ethanol

Guidance literature:: Multi-step reaction with 5 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

5: 97 percent / diisobutylaluminum hydride / toluene / 0.67 h / 0 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; diisobutylaluminium hydride; pyridinium chlorochromate; 2-hydroxynitrobenzene; In tetrahydrofuran; methanol; dichloromethane; toluene; 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

: 712280-95-0
2-{(1'S,4'R,6'S)-1'-[3'',4''-(methylenedioxy)phenyl]-6'-benzyloxy-4'-(tert-butyldimethylsilyloxy)-2'-cyclohexenyl}ethanol

Guidance literature:: Multi-step reaction with 3 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

3: 97 percent / diisobutylaluminum hydride / toluene / 0.67 h / 0 °C

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