(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

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]dodecane
CAS No.:815598-54-0
Molecular Formula:C₄₇H₇₀O₈Si
Molecular Weight:791.153
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]dodecane

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]dodecane

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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]dodecane

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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]dodecane

There total 9 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]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:

: 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

: 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

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; tetrabutyl ammonium fluoride; sec.-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; 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

: 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

Guidance literature:: Multi-step reaction with 8 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

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

Reference yield:

: 855301-65-4
(1R,2S,3S,5R,6S,7S,8R,9S)-2,6-bis(benzyloxy)-3-(3-butenyl)-5-(t-butyldimethylsilyloxy)-7,9-(isopropylidenedioxy)-8-(methoxymethoxymethyl)-4,4-dimethyl-12-methylenebicyclo[6.4.0]dodecan-3-ol

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / imidazole / dimethylformamide / 0.17 h / 20 °C

2: 99 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C

With 1H-imidazole; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.78.677