Technology Process of tert-butyl {(4R,6E,8R,10E,12R,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate
There total 14 articles about tert-butyl {(4R,6E,8R,10E,12R,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate 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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1274953-69-3
tert-butyl {(4R,6E,8R,10E,12R,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate
- Guidance literature:
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N,N,N-tributylbutan-1-aminium trifluoro(propa-1,2-dien-1-yl)borate;
With
chloro-trimethyl-silane; lithium (S)-B-H2-(10)-trimethylsilyl-9-borabicyclo[3.3.2]decane;
In
dichloromethane; toluene;
at -78 - -30 ℃;
Inert atmosphere;
(3S,5S)-3,5-bis-(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptane-1-al;
In
dichloromethane; toluene;
at -78 ℃;
for 4h;
Inert atmosphere;
tert-butyl ((4R,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-8-oxooct-6-en-1-yl)carbamate;
Further stages;
DOI:10.1016/j.tet.2011.06.008
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1274953-69-3
tert-butyl {(4R,6E,8R,10E,12R,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate
- Guidance literature:
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With
potassium dihydrogenphosphate; sodium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene;
at 20 ℃;
for 24h;
pH=7;
optical yield given as %de;
Inert atmosphere;
DOI:10.1021/ol2003836
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1274953-69-3
tert-butyl {(4R,6E,8R,10E,12R,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate
- Guidance literature:
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Multi-step reaction with 5 steps
1: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere
2: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water; tert-butyl alcohol / 5 h / Inert atmosphere
3: diethyl ether; dichloromethane; toluene / 4 h / -78 °C / Inert atmosphere
4: boron trifluoride diethyl etherate / diethyl ether; dichloromethane; toluene / 4 h / -78 °C / Inert atmosphere
5: potassium dihydrogenphosphate; sodium hydroxide / tetrahydrofuran; methanol; dichloromethane; water; toluene / 24 h / 20 °C / pH 7 / Inert atmosphere
With
1H-imidazole; 2,6-dimethylpyridine; sodium periodate; potassium dihydrogenphosphate; osmium(VIII) oxide; boron trifluoride diethyl etherate; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/ol2003836