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

Base Information

Chemical Name: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
CAS No.:712280-96-1
Molecular Formula:C₄₀H₅₃NO₈SSi
Molecular Weight:736.014
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 7 articles about 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 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: 98.0%

: 18303-04-3
N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

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

: 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:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1039/b402762k

Reference yield:

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

: 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 6 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

6: 98 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; diisobutylaluminium hydride; triphenylphosphine; pyridinium chlorochromate; 2-hydroxynitrobenzene; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; 3: Luche reduction / 4: Johnson-Claisen rearrangement / 6: Mitsunobu amination;
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

: 712280-96-1
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 4 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

4: 98 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C

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