Technology Process of (3E,5E,15E,21E)-(8R,9R,10R,11R,14S,18R,20R,24S)-10-(tert-Butyl-dimethyl-silanyloxy)-24-[(1R,2S,3S)-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-4-trityloxy-butyl]-8-hydroxy-14,20-dimethoxy-9,11,18-trimethyl-oxacyclotetracosa-3,5,15,21-tetraen-2-one
There total 30 articles about (3E,5E,15E,21E)-(8R,9R,10R,11R,14S,18R,20R,24S)-10-(tert-Butyl-dimethyl-silanyloxy)-24-[(1R,2S,3S)-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-4-trityloxy-butyl]-8-hydroxy-14,20-dimethoxy-9,11,18-trimethyl-oxacyclotetracosa-3,5,15,21-tetraen-2-one 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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423772-18-3
(3E,5E,15E,21E)-(8R,9R,10R,11R,14S,18R,20R,24S)-10-(tert-Butyl-dimethyl-silanyloxy)-24-[(1R,2S,3S)-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-4-trityloxy-butyl]-8-hydroxy-14,20-dimethoxy-9,11,18-trimethyl-oxacyclotetracosa-3,5,15,21-tetraen-2-one
- Guidance literature:
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With
2,6-dimethylpyridine; silver nitrate;
In
tetrahydrofuran; water;
at 30 ℃;
for 22h;
DOI:10.1016/S0040-4020(01)01206-6
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423772-18-3
(3E,5E,15E,21E)-(8R,9R,10R,11R,14S,18R,20R,24S)-10-(tert-Butyl-dimethyl-silanyloxy)-24-[(1R,2S,3S)-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-4-trityloxy-butyl]-8-hydroxy-14,20-dimethoxy-9,11,18-trimethyl-oxacyclotetracosa-3,5,15,21-tetraen-2-one
- Guidance literature:
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Multi-step reaction with 19 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
13: 83 percent / C6H4(COO)I(OAc)3 / CH2Cl2 / 0.25 h / 20 °C
14: 94 percent / LDA / tetrahydrofuran / -48 - 0 °C
15: 91 percent / HF-pyridine; pyridine / tetrahydrofuran / 1 h / 20 °C
16: LiOH / methanol; H2O / 20 °C
17: 49 percent / 2,4,6-trichlorobenzoyl chloride; DMAP; Et3N / CH2Cl2 / 20 °C
18: 86 percent / imidazole / dimethylformamide / 16 h / 60 °C
19: 86 percent / AgNO3; 2,6-lutidine / tetrahydrofuran; H2O / 22 h / 30 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium hydroxide; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; n-butyllithium; sodium amalgam; tributylphosphine; C6H4(COO)I(OAc)3; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; silver nitrate; triethylamine; 3-chloro-benzenecarboperoxoic acid; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide;
palladium dihydroxide;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)01206-6
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423772-18-3
(3E,5E,15E,21E)-(8R,9R,10R,11R,14S,18R,20R,24S)-10-(tert-Butyl-dimethyl-silanyloxy)-24-[(1R,2S,3S)-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-4-trityloxy-butyl]-8-hydroxy-14,20-dimethoxy-9,11,18-trimethyl-oxacyclotetracosa-3,5,15,21-tetraen-2-one
- Guidance literature:
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Multi-step reaction with 18 steps
1: 80 percent / Me4NBH(OAc)3 / acetonitrile; acetic acid / 25 h / -20 °C
2: 100 percent / hydrogen / 20 percent Pd(OH)2/C / dioxane / 15 h / 20 °C
3: 93 percent / PBu3 / dimethylformamide / 1.5 h / 20 °C
4: 100 percent / Bu4NF / tetrahydrofuran / 3 h / 20 °C
5: 96 percent / pyridine / 11.5 h / 50 °C
6: 93 percent / imidazole / dimethylformamide / 1.5 h / 50 °C
7: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 / 1.5 h / 20 °C
8: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
9: DMAP / pyridine / 3.5 h / 20 °C
10: 5 percent Na-Hg; NaH2PO4 / methanol / 35 h / 0 °C
11: 96 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C
12: 83 percent / C6H4(COO)I(OAc)3 / CH2Cl2 / 0.25 h / 20 °C
13: 94 percent / LDA / tetrahydrofuran / -48 - 0 °C
14: 91 percent / HF-pyridine; pyridine / tetrahydrofuran / 1 h / 20 °C
15: LiOH / methanol; H2O / 20 °C
16: 49 percent / 2,4,6-trichlorobenzoyl chloride; DMAP; Et3N / CH2Cl2 / 20 °C
17: 86 percent / imidazole / dimethylformamide / 16 h / 60 °C
18: 86 percent / AgNO3; 2,6-lutidine / tetrahydrofuran; H2O / 22 h / 30 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium hydroxide; sodium dihydrogenphosphate; n-butyllithium; sodium amalgam; tributylphosphine; C6H4(COO)I(OAc)3; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; silver nitrate; triethylamine; 3-chloro-benzenecarboperoxoic acid; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide;
palladium dihydroxide;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)01206-6