(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

Base Information

Chemical Name:(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
CAS No.:815598-51-7
Molecular Formula:C₄₁H₆₀O₈Si
Molecular Weight:709.008
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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: 95.0%

: 815598-62-0
(1R,2S,3S,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-ol

: 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

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃;
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

: 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

Guidance literature:: Multi-step reaction with 4 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

With lithium aluminium tetrahydride; phosphate buffer; sulfuric acid; camphor-10-sulfonic acid; water; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1246/bcsj.78.677

Reference yield:

: 815598-50-6
(1R,2S,3S,4R,6R,7S,8R,12S)-3,7-bis(benzyloxy)-4-(t-butyldimethylsilyloxy)-2,12-(isopropylidenedioxy)-6-(4-methoxybenzyloxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecane

: 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

Guidance literature:: Multi-step reaction with 2 steps

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

2: 95 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

With phosphate buffer; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1246/bcsj.78.677