(1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

Base Information

Chemical Name:(1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one
CAS No.:855301-80-3
Molecular Formula:C₄₇H₆₈O₈Si
Molecular Weight:789.138
Hs Code.:

(1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

Synonyms:(1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

Suppliers and Price of (1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

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Chemical Property of (1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

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Technology Process of (1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

There total 11 articles about (1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-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: 97.0%

: 815598-54-0
(1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecane

: 855301-80-3
(1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 ℃;
DOI:10.1246/cl.2004.1412

Reference yield:

: 815598-51-7
(1R,2S,5R,6S,7S,8R,9S)-2,6-bis(benzyloxy)-5-(t-butyldimethylsilyloxy)-7,9-(isopropylidenedioxy)-8-(methoxymethoxymethyl)-4,4-dimethyl-12-methylenebicyclo[6.4.0]dodecan-3-one

: 855301-80-3
(1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / s-butyllithium / benzene; cyclohexane / 1 h / 0 °C

2: 80 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 50 °C

3: 100 percent / imidazole / dimethylformamide / 0.17 h / 20 °C

4: 99 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C

5: 97 percent / NaHCO₃; Dess-Martim periodinane / CH₂Cl₂ / 0.33 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; sec.-butyllithium; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide; benzene;
DOI:10.1246/bcsj.78.677

Reference yield:

: 677751-25-6
(1R,3R,4R,6R,7S,8R,12S)-3,7-bis(benzyloxy)-4-(t-butyldimethylsilyloxy)-12-hydroxy-1-methoxymethoxymethyl-6-(4-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

: 855301-80-3
(1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one

Guidance literature:: Multi-step reaction with 9 steps

1: 81 percent / LiAlH₄; sulfuric acid; water / tetrahydrofuran; toluene / 2 h / -23 °C

2: 92 percent / camphorsulfonic acid / CH₂Cl₂ / 5 h / 20 °C

3: 100 percent / phosphate buffer; 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1.5 h / 0 °C / pH 7

4: 95 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

5: 97 percent / s-butyllithium / benzene; cyclohexane / 1 h / 0 °C

6: 80 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 50 °C

7: 100 percent / imidazole / dimethylformamide / 0.17 h / 20 °C

8: 99 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C

9: 97 percent / NaHCO₃; Dess-Martim periodinane / CH₂Cl₂ / 0.33 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; phosphate buffer; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; sec.-butyllithium; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1246/bcsj.78.677