Technology Process of 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
There total 20 articles about 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 which
guide to synthetic route it.
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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
- Guidance literature:
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With
sodium dihydrogenphosphate; sodium amalgam;
In
methanol;
at 0 ℃;
for 35h;
DOI:10.1016/S0040-4020(01)01206-6
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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
- Guidance literature:
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Multi-step reaction with 11 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
With
pyridine; 1H-imidazole; dmap; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; n-butyllithium; sodium amalgam; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; 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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423772-12-7
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
- Guidance literature:
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Multi-step reaction with 9 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
With
pyridine; 1H-imidazole; dmap; sodium dihydrogenphosphate; n-butyllithium; sodium amalgam; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; 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
