Technology Process of (R)-2-tert-butoxycarbonylamino-3-methyl-butyric acid (2R,3S,4R,5R,6S)-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-3,4,5-trihydroxy-tetrahydropyran-2-ylmethyl ester
There total 10 articles about (R)-2-tert-butoxycarbonylamino-3-methyl-butyric acid (2R,3S,4R,5R,6S)-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-3,4,5-trihydroxy-tetrahydropyran-2-ylmethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
palladium(II) hydroxide;
In
methanol; ethyl acetate;
at 20 ℃;
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: trifluoroacetic acid; trifluorormethanesulfonic acid; triethylsilane / 0.42 h / 20 °C
2.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 1 h / -78 °C
2.2: 1 h / -78 °C
2.3: 16 h / 20 °C
3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 4 h / 10 °C
4.1: dmap; pyridine / dichloromethane / 2 h / 20 °C
5.1: tricyclohexylphosphine; potassium phosphate / toluene; water / 0.75 h
5.2: Reflux
6.1: lithium hydroxide monohydrate / water; tetrahydrofuran; methanol
7.1: dmap; pyridine / 16 h / 20 - 80 °C
8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 20 °C
8.2: 0 - 20 °C
9.1: aluminum (III) chloride / dichloromethane; diethyl ether / 2 h / 0 - 20 °C
10.1: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 0.5 h / 20 °C
10.2: 0 - 20 °C
11.1: palladium(II) hydroxide / ethyl acetate; methanol / 20 °C
With
pyridine; triethylsilane; dmap; aluminum (III) chloride; potassium phosphate; n-butyllithium; lithium hydroxide monohydrate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; palladium(II) hydroxide; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; tricyclohexylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C
2.1: trifluoroacetic acid; trifluorormethanesulfonic acid; triethylsilane / 0.42 h / 20 °C
3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 1 h / -78 °C
3.2: 1 h / -78 °C
3.3: 16 h / 20 °C
4.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 4 h / 10 °C
5.1: dmap; pyridine / dichloromethane / 2 h / 20 °C
6.1: tricyclohexylphosphine; potassium phosphate / toluene; water / 0.75 h
6.2: Reflux
7.1: lithium hydroxide monohydrate / water; tetrahydrofuran; methanol
8.1: dmap; pyridine / 16 h / 20 - 80 °C
9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 20 °C
9.2: 0 - 20 °C
10.1: aluminum (III) chloride / dichloromethane; diethyl ether / 2 h / 0 - 20 °C
11.1: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 0.5 h / 20 °C
11.2: 0 - 20 °C
12.1: palladium(II) hydroxide / ethyl acetate; methanol / 20 °C
With
pyridine; triethylsilane; dmap; aluminum (III) chloride; potassium phosphate; n-butyllithium; lithium hydroxide monohydrate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; palladium(II) hydroxide; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; tricyclohexylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;