Technology Process of (2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane
There total 32 articles about (2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane 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:
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476622-77-2
(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-3,5,9,11,13-pentamethyltetradecan-7-on
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251099-50-0
(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane
- Guidance literature:
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With
potassium hexamethylsilazane;
In
tetrahydrofuran; toluene;
at 50 ℃;
for 2h;
DOI:10.1021/ja020853m
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251099-50-0
(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane
- Guidance literature:
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(2R,3R,4S,5R,6S)-1-iodo-7-(tert-butyldiphenylsilyloxy)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-heptane;
With
tert.-butyl lithium;
In
tetrahydrofuran;
at -78 ℃;
for 0.5h;
With
zinc(II) chloride;
In
tetrahydrofuran;
at -78 ℃;
for 0.25h;
(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate;
With
tetrakis(triphenylphosphine) palladium(0); lithium chloride;
at -78 - 20 ℃;
for 0.75h;
DOI:10.1021/ja992370x
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251099-50-0
(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane
- Guidance literature:
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Multi-step reaction with 11 steps
1.1: 92 percent / aq. HCl / methanol / 20 °C
2.1: 2,4-lutidine / CH2Cl2 / -78 °C
3.1: O3 / methanol; pyridine
3.2: Me2S / methanol; pyridine
4.1: 87 percent / TiCl4 / CH2Cl2 / -78 - -30 °C
5.1: HF*pyridine; pyridine / tetrahydrofuran / 1 h / 0 °C
6.1: 2.29 g / imidazole / dimethylformamide / 4 h / 20 °C
7.1: 99 percent / p-toluenesulfonic acid monohydrate / 0.75 h / 20 °C
8.1: O3; pyridine / methanol / -78 °C
8.2: Me2S / methanol / 4 h / -78 - 20 °C
9.1: 1.09 g / NaBH4 / methanol / 0.5 h / 0 °C
10.1: 98 percent / I2; triphenylphosphine; imidazole / CH2Cl2 / 12.25 h / 0 - 20 °C
11.1: t-BuLi / pentane / 0.5 h / -78 - 20 °C
11.2: ZnCl2 / tetrahydrofuran; pentane / 0.25 h / -78 °C
11.3: 82 percent / Pd(PPh3)4; LiCl / tetrahydrofuran; pentane / -78 - 0 °C
With
pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; 2,4-lutidine; iodine; tert.-butyl lithium; titanium tetrachloride; pyridine hydrogenfluoride; ozone; triphenylphosphine;
toluene-4-sulfonic acid;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ja020853m
