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

Base Information

Chemical Name:(1S,2S,3S,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(3-butenyl)-6-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one
CAS No.:222726-99-0
Molecular Formula:C₄₃H₆₂O₆Si
Molecular Weight:703.047
Hs Code.:

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

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

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

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

There total 14 articles about (1S,2S,3S,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(3-butenyl)-6-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one 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: 85.0%

: 202341-11-5
(1S,2S,3R,4R,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(3-butenyl)-6-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-4-ol

: 222726-99-0
(1S,2S,3S,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(3-butenyl)-6-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane; acetonitrile; Ambient temperature;
DOI:10.1246/cl.1998.1

Reference yield:

: 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

: 222726-99-0
(1S,2S,3S,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(3-butenyl)-6-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / PDC / CH₂Cl₂ / 16 h / 20 °C

2.1: s-BuLi / cyclohexane / 0.42 h / -23 °C

2.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C

3.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C

4.1: 100 percent / pyridine / toluene / 0.67 h / 0 °C

5.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.67 h / -45 °C

6.1: 85 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂; acetonitrile / 0.75 h / 20 °C

With pyridine; dipyridinium dichromate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sec.-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; cyclohexane; toluene; acetonitrile; 1.1: Oxidation / 2.1: Metallation / 2.2: Alkylation / 3.1: Substitution / 4.1: Etherification / 5.1: Methylation / 6.1: Oxidation;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

: 194420-20-7
(1R,2S,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-one

: 222726-99-0
(1S,2S,3S,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(3-butenyl)-6-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: s-BuLi / cyclohexane / 0.42 h / -23 °C

1.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C

2.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C

3.1: 100 percent / pyridine / toluene / 0.67 h / 0 °C

4.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.67 h / -45 °C

5.1: 85 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂; acetonitrile / 0.75 h / 20 °C

With pyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sec.-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; cyclohexane; toluene; acetonitrile; 1.1: Metallation / 1.2: Alkylation / 2.1: Substitution / 3.1: Etherification / 4.1: Methylation / 5.1: Oxidation;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f