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

Base Information

Chemical Name:(1R,2S,3R,5R,6S,7S,8S,9S)-2,6-Dibenzyloxy-5-(tert-butyldimethylsiloxy)-7,9-(isopropylidenedioxy)-4,4,8-trimethyl-12-methylenebicyclo[6.4.0]dodecan-3-ol
CAS No.:222726-95-6
Molecular Formula:C₃₉H₅₈O₆Si
Molecular Weight:650.971
Hs Code.:

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

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

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

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

There total 8 articles about (1R,2S,3R,5R,6S,7S,8S,9S)-2,6-Dibenzyloxy-5-(tert-butyldimethylsiloxy)-7,9-(isopropylidenedioxy)-4,4,8-trimethyl-12-methylenebicyclo[6.4.0]dodecan-3-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: 97.0%

: 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

: 222726-95-6
(1R,2S,3R,5R,6S,7S,8S,9S)-2,6-Dibenzyloxy-5-(tert-butyldimethylsiloxy)-7,9-(isopropylidenedioxy)-4,4,8-trimethyl-12-methylenebicyclo[6.4.0]dodecan-3-ol

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; Ambient temperature;
DOI:10.1246/cl.1998.1

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

: 222726-95-6
(1R,2S,3R,5R,6S,7S,8S,9S)-2,6-Dibenzyloxy-5-(tert-butyldimethylsiloxy)-7,9-(isopropylidenedioxy)-4,4,8-trimethyl-12-methylenebicyclo[6.4.0]dodecan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 97 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C

With aluminium hydride; camphor-10-sulfonic acid; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; toluene; 1: Reduction / 2: Etherification / 3: Hydrolysis;
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

: 222726-95-6
(1R,2S,3R,5R,6S,7S,8S,9S)-2,6-Dibenzyloxy-5-(tert-butyldimethylsiloxy)-7,9-(isopropylidenedioxy)-4,4,8-trimethyl-12-methylenebicyclo[6.4.0]dodecan-3-ol

Guidance literature:: Multi-step reaction with 8 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

8.1: 97 percent / DDQ; H₂O / 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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 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 / 8.1: Hydrolysis;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f