(1S,2S,3S,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane

Base Information

Chemical Name:(1S,2S,3S,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane
CAS No.:194420-19-4
Molecular Formula:C₄₇H₆₆O₇Si
Molecular Weight:771.122
Hs Code.:

(1S,2S,3S,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane

Synonyms:(1S,2S,3S,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane

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Chemical Property of (1S,2S,3S,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane

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Technology Process of (1S,2S,3S,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane

There total 7 articles about (1S,2S,3S,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane 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:

: 194420-17-2
2α,10β-dibenzyloxy-11β-(t-butyldimethylsiloxy)-7β-hydroxy-1α-(p-methoxybenzyloxy)-8β,15,15-trimethyl-4-methylene-trans-bicyclo[6.4.0]dodecan-9-one

: 194420-19-4
(1S,2S,3S,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / AlH₃ / toluene; tetrahydrofuran / 2 h / -78 °C

2: 100 percent / CSA / CH₂Cl₂ / 1 h / 20 °C

With aluminium hydride; camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane; toluene; 1: Reduction / 2: Etherification;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

: 64180-78-5
4-bromopent-4-en-1-ol

: 194420-19-4
(1S,2S,3S,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane

Guidance literature:: Multi-step reaction with 7 steps

1.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C

2.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C

2.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C

2.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C

3.1: 97 percent / HCl; H₂O / tetrahydrofuran / 0.83 h / 0 °C

4.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 90 percent / MeONa / methanol / 1 h / 0 °C

6.1: 94 percent / AlH₃ / toluene; tetrahydrofuran / 2 h / -78 °C

7.1: 100 percent / CSA / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; aluminium hydride; hydrogenchloride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; water; tert.-butyl lithium; sodium methylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; 1.1: Etherification / 2.1: Metallation / 2.2: Substitution / 2.3: Addition / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Cycloaddition / 6.1: Reduction / 7.1: Etherification;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

: 35804-44-5
ethyl 4-bromo-4-pentenoate

: 194420-19-4
(1S,2S,3S,4R,6R,7S,8R,12S)-3,7-Dibenzyloxy-4-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-6-(p-methoxybenzyloxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane

Guidance literature:: Multi-step reaction with 8 steps

1.1: LiAlH₄ / tetrahydrofuran / 0.67 h / 0 °C

2.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C

3.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C

3.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C

3.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C

4.1: 97 percent / HCl; H₂O / tetrahydrofuran / 0.83 h / 0 °C

5.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 90 percent / MeONa / methanol / 1 h / 0 °C

7.1: 94 percent / AlH₃ / toluene; tetrahydrofuran / 2 h / -78 °C

8.1: 100 percent / CSA / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; aluminium hydride; hydrogenchloride; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; water; tert.-butyl lithium; sodium methylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; 1.1: Reduction / 2.1: Etherification / 3.1: Metallation / 3.2: Substitution / 3.3: Addition / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Cycloaddition / 7.1: Reduction / 8.1: Etherification;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f