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

Base Information

• Chemical Name: (1R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol
• CAS No.: 712281-01-1
• Molecular Formula: C₂₆H₃₄O₅Si
• Molecular Weight: 454.638
• Mol file: 712281-01-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1R,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%

(3,4-methylenedioxy)phenylmagnesium bromide (17680-04-5) + (4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone (581060-33-5) → (1R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol (712281-01-1) + (1S,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol (712280-91-6)

Guidance literature:

In tetrahydrofuran; at -100 ℃; for 1h;

DOI:10.1039/b402762k

Reference yield:

(1R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol (712281-01-1) → (4S,6R)-4-benzyloxy-6-(tert-butyldimethylsilyloxy)-3-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-one (712280-92-7)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 20 ℃;

DOI:10.1039/b402762k

Reference yield:

(1R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-1-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol (712281-01-1) → (1R,4S,6R)-4-benzyloxy-6-(tert-butyldimethylsilyloxy)-3-[3',4'-(methylenedioxy)phenyl]-2-cyclohexen-1-ol (712280-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.65 g / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

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

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; 2: Luche reduction;

DOI:10.1039/b402762k

upstream raw materials:

(3,4-methylenedioxy)phenylmagnesium bromide

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

Downstream raw materials:

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

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

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

N-(tert-butoxycarbonyl)-N-{2-(1'S,4'R,6'S)-1'-[3,4-(methylenedioxy)phenyl]-4'-(tert-butyldimethylsilyloxy)-2'-cyclohexenyl}ethyl amine