Technology Process of (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dien-1-ol
There total 20 articles about (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dien-1-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:
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423772-12-7
2,2-Dimethyl-propionic acid (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienyl ester
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423772-13-8
(10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dien-1-ol
- Guidance literature:
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With
diisobutylaluminium hydride;
In
hexane; dichloromethane;
at -78 ℃;
for 1h;
DOI:10.1016/S0040-4020(01)01206-6
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423772-13-8
(10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dien-1-ol
- Guidance literature:
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Multi-step reaction with 12 steps
1: 83 percent / Sn(OTf)2; Et3N / CH2Cl2 / -78 - -20 °C
2: 80 percent / Me4NBH(OAc)3 / acetonitrile; acetic acid / 25 h / -20 °C
3: 100 percent / hydrogen / 20 percent Pd(OH)2/C / dioxane / 15 h / 20 °C
4: 93 percent / PBu3 / dimethylformamide / 1.5 h / 20 °C
5: 100 percent / Bu4NF / tetrahydrofuran / 3 h / 20 °C
6: 96 percent / pyridine / 11.5 h / 50 °C
7: 93 percent / imidazole / dimethylformamide / 1.5 h / 50 °C
8: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 / 1.5 h / 20 °C
9: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
10: DMAP / pyridine / 3.5 h / 20 °C
11: 5 percent Na-Hg; NaH2PO4 / methanol / 35 h / 0 °C
12: 96 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C
With
pyridine; 1H-imidazole; dmap; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; n-butyllithium; sodium amalgam; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; tetramethylammonium triacetoxyborohydride;
palladium dihydroxide;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)01206-6
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423772-13-8
(10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dien-1-ol
- Guidance literature:
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Multi-step reaction with 10 steps
1: 100 percent / hydrogen / 20 percent Pd(OH)2/C / dioxane / 15 h / 20 °C
2: 93 percent / PBu3 / dimethylformamide / 1.5 h / 20 °C
3: 100 percent / Bu4NF / tetrahydrofuran / 3 h / 20 °C
4: 96 percent / pyridine / 11.5 h / 50 °C
5: 93 percent / imidazole / dimethylformamide / 1.5 h / 50 °C
6: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 / 1.5 h / 20 °C
7: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
8: DMAP / pyridine / 3.5 h / 20 °C
9: 5 percent Na-Hg; NaH2PO4 / methanol / 35 h / 0 °C
10: 96 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C
With
pyridine; 1H-imidazole; dmap; sodium dihydrogenphosphate; n-butyllithium; sodium amalgam; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid;
palladium dihydroxide;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01206-6
