Technology Process of (2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid [2-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1-trimethylsilanyl-hexyl]-amide
There total 11 articles about (2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid [2-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1-trimethylsilanyl-hexyl]-amide which
guide to synthetic route it.
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synthetic route:
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(2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid [2,6-bis-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyl-hexyl]-amide
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443123-84-0
(2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid [2-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1-trimethylsilanyl-hexyl]-amide
- Guidance literature:
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With
camphor-10-sulfonic acid;
In
methanol; dichloromethane;
at 0 ℃;
for 5h;
DOI:10.1016/S0040-4039(02)00289-7
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443123-84-0
(2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid [2-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1-trimethylsilanyl-hexyl]-amide
- Guidance literature:
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Multi-step reaction with 11 steps
1: (COCl)2; Et3N; DMSO / CH2Cl2 / -78 °C
2: PPh3; Et3N / CH2Cl2 / 0.5 h / 0 °C
3: nBuLi / tetrahydrofuran / 0.5 h / -78 °C
4: camphorsulfonic acid / methanol; CH2Cl2 / 0.5 h / 0 °C
5: H2 / Lindlar's catalyst / hexane
6: 79 percent / mCPBA / CH2Cl2 / 0.75 h / 0 - 20 °C
7: 88 percent / NaN3; NH4Cl / methanol; H2O / 15 h / 0 - 20 °C
8: LiAlH4 / diethyl ether / 2 h / 0 - 20 °C
9: EDCI; HOBt / CH2Cl2 / 5.25 h / 0 - 20 °C
10: 2,6-lutidine / CH2Cl2 / 0.25 h / 0 °C
11: camphorsulfonic acid / methanol; CH2Cl2 / 5 h / 0 °C
With
2,6-dimethylpyridine; lithium aluminium tetrahydride; n-butyllithium; sodium azide; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; ammonium chloride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water;
1: Swern oxidation;
DOI:10.1016/S0040-4039(02)00289-7
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443123-84-0
(2E,4E,10E)-(6S,7S,8R,9S)-7,9-Dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoic acid [2-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1-trimethylsilanyl-hexyl]-amide
- Guidance literature:
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Multi-step reaction with 10 steps
1: PPh3; Et3N / CH2Cl2 / 0.5 h / 0 °C
2: nBuLi / tetrahydrofuran / 0.5 h / -78 °C
3: camphorsulfonic acid / methanol; CH2Cl2 / 0.5 h / 0 °C
4: H2 / Lindlar's catalyst / hexane
5: 79 percent / mCPBA / CH2Cl2 / 0.75 h / 0 - 20 °C
6: 88 percent / NaN3; NH4Cl / methanol; H2O / 15 h / 0 - 20 °C
7: LiAlH4 / diethyl ether / 2 h / 0 - 20 °C
8: EDCI; HOBt / CH2Cl2 / 5.25 h / 0 - 20 °C
9: 2,6-lutidine / CH2Cl2 / 0.25 h / 0 °C
10: camphorsulfonic acid / methanol; CH2Cl2 / 5 h / 0 °C
With
2,6-dimethylpyridine; lithium aluminium tetrahydride; n-butyllithium; sodium azide; camphor-10-sulfonic acid; hydrogen; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water;
DOI:10.1016/S0040-4039(02)00289-7