(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

Base Information

Chemical Name:(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
CAS No.:677751-25-6
Molecular Formula:C₄₆H₆₄O₉Si
Molecular Weight:789.094
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 1 articles about (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 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: 76.0%

: 107-30-2
chloromethyl methyl ether

: 677751-22-3
(1R,3R,4R,6R,7S,8R,12S)-3,7-bis(benzyloxy)-4-(t-butyldimethylsilyloxy)-12-hydroxy-1-hydroxymethyl-6-(4-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one

: 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

Guidance literature:: With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1246/cl.2004.124

Reference yield: 81.0%

: 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

: 855301-78-9
(1R,2S,3S,4R,6R,7S,8R,12S)-3,7-bis(benzyloxy)-4-(t-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecane-2,12-diol

Guidance literature:: With aluminium hydride; In tetrahydrofuran; at -23 ℃;
DOI:10.1246/cl.2004.1412

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

: 855301-76-7
(1S,4aR,5S,6S,9R,10R,11S,12S,12aR)-6-(cyclohexyldimethylsilyloxy)-1,12-(isopropylidenedioxy)-12a-(methoxymethoxymethyl)-9,13,13-trimethyl-4-methylenetetradecahydro-6,10-methanobenzocyclodecene-5,9,10,11-tetrol

Guidance literature:: Multi-step reaction with 12 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

10: 83 percent / palladium(II) chloride; H₂O / dimethylformamide / 3.5 h / 20 °C

11: 64 percent / titanium(II) chloride; lithium aluminium hydride / tetrahydrofuran / 0.33 h / 40 °C

12: 96 percent / sodium; ammonia / tetrahydrofuran / -78 - -48 °C

With 1H-imidazole; lithium aluminium tetrahydride; phosphate buffer; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; water; sec.-butyllithium; sodium; titanium chloride; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride; 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