(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

Base Information

Chemical Name:(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
CAS No.:202341-11-5
Molecular Formula:C₄₃H₆₄O₆Si
Molecular Weight:705.063
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 13 articles about (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 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: 96.0%

: 917-54-4
methyllithium

: 202341-06-8
(1S,2S,3S,4R,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(3-butenyl)-4,6-(tert-butylmethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane

: 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

Guidance literature:: In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; at -45 ℃; for 0.666667h;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

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

: 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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 202340-82-7
(1R,2S,3S,5R,6R,7S,8S,9S)-2,6-Dibenzyloxy-3-(3-butenyl)-7,9-(isopropylidenedioxy)-4,4,8-trimethyl-12-methylenebicyclo[6.4.0]dodecan-3,5-diol

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / pyridine / toluene / 0.67 h / 0 °C

2: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.67 h / -45 °C

With pyridine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; toluene; 1: Etherification / 2: Methylation;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f