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

Base Information

Chemical Name:(1S,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol
CAS No.:712280-91-6
Molecular Formula:C₂₆H₃₄O₅Si
Molecular Weight:454.638
Hs Code.:

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

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Chemical Property of (1S,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol

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Technology Process of (1S,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol

There total 1 articles about (1S,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-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: 68.0%

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

: 581060-33-5
(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone

: 712281-01-1
(1R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol

: 712280-91-6
(1S,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol

Guidance literature:: In tetrahydrofuran; at -100 ℃; for 1h;
DOI:10.1039/b402762k

Reference yield:

: 712280-91-6
(1S,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol

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

Guidance literature:: With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1039/b402762k

Reference yield:

: 712280-91-6
(1S,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol

: 712280-96-1
N-(tert-butoxycarbonyl)-N-{2-(1'S,4'R,6'S)-1'-[3,4-(methylenedioxy)phenyl]-6'-benzyloxy-4'-(tert-butyldimethylsilyloxy)-cyclohex-2'-enyl}ethyl-N-(p-toluenesulfonyl)-amine

Guidance literature:: Multi-step reaction with 5 steps

1: 1.90 g / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / 20 °C

2: 1.87 g / NaBH₄; CeCl₃*7H₂O / CH₂Cl₂ / 0.5 h / -78 °C

3: 60 percent / propionic acid; 4 Angstroem molecular sieves / 24 h / 130 °C

4: 97 percent / DIBAL-H / toluene / 0.67 h / 0 °C

5: 98 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 1 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; diisobutylaluminium hydride; propionic acid; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; toluene; 2: Luche reduction / 3: Claisen rearrangement;
DOI:10.1039/b402762k