Technology Process of 5,7,21-Trioxa-2,22-disilatetracos-10-en-18-one,
20-[2-[bis(4-methoxyphenyl)phenylmethoxy]ethyl]-16-hydroxy-2,2,11,15,
17,19,19,22,22,23,23-undecamethyl-8-[(1E)-1-methyl-2-(2-methyl-4-thi
azolyl)ethenyl]-, (8S,10Z,15S,16S,17R,20S)-
There total 29 articles about 5,7,21-Trioxa-2,22-disilatetracos-10-en-18-one,
20-[2-[bis(4-methoxyphenyl)phenylmethoxy]ethyl]-16-hydroxy-2,2,11,15,
17,19,19,22,22,23,23-undecamethyl-8-[(1E)-1-methyl-2-(2-methyl-4-thi
azolyl)ethenyl]-, (8S,10Z,15S,16S,17R,20S)- 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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396092-46-9
(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3-tert-butyldimethylsilyloxy-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one
- Guidance literature:
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(5S)-7-[di-(4-methoxyphenyl)(phenyl)methoxy]-5-tert-butyldimethylsilyloxy-4,4-dimethylheptan-3-one;
With
n-butyllithium; lithium diisopropyl amide;
In
tetrahydrofuran; hexane;
at -78 - 40 ℃;
for 1.5h;
(+)-(2S,6Z,9S,10E)-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxymethoxy)undeca-6,10-dienal;
In
tetrahydrofuran; hexane;
at -78 ℃;
for 0.0333333h;
DOI:10.1039/c2ob26310f
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396092-46-9
(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3-tert-butyldimethylsilyloxy-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one
- Guidance literature:
-
Multi-step reaction with 14 steps
1.1: 78 percent / i-Pr2EtN
2.1: Bu3SnH; AIBN
2.2: SnBr4 / -78 °C
3.1: 80 percent / pyridine
4.1: 59 percent / Bu3SnH; AIBN
5.1: 91 percent / DDQ
6.1: 97 percent / Bu4NF
7.1: Dess-Martin periodinane
8.1: 99 percent / Dess-Martin periodinane
9.1: 74 percent / n-BuLi
10.1: DIBAL-H
11.1: Dess-Martin periodinane
12.1: 67 percent / Li(i-Pr)2N / -78 °C
With
pyridine; n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide;
8.1: Dess-Martin oxidation / 10.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4039(01)01795-6
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396092-46-9
(3S,6R,7S,8S,15S,12Z,16E)-1-[di-(4-methoxyphenyl)(phenyl)-methoxy]-3-tert-butyldimethylsilyloxy-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-15-(2-trimethylsilylethoxy)-methoxyheptadeca-12,16-dien-5-one
- Guidance literature:
-
Multi-step reaction with 15 steps
1.1: imid.
2.1: 78 percent / i-Pr2EtN
3.1: Bu3SnH; AIBN
3.2: SnBr4 / -78 °C
4.1: 80 percent / pyridine
5.1: 59 percent / Bu3SnH; AIBN
6.1: 91 percent / DDQ
7.1: 97 percent / Bu4NF
8.1: Dess-Martin periodinane
9.1: 99 percent / Dess-Martin periodinane
10.1: 74 percent / n-BuLi
11.1: DIBAL-H
12.1: Dess-Martin periodinane
13.1: 67 percent / Li(i-Pr)2N / -78 °C
With
pyridine; 1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide;
9.1: Dess-Martin oxidation / 11.1: Dess-Martin oxidation / 14.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4039(01)01795-6