15-O-benzyl-13-deoxy-isatisine A

Base Information

Chemical Name:15-O-benzyl-13-deoxy-isatisine A
CAS No.:1402730-62-4
Molecular Formula:C₂₉H₂₄N₂O₅
Molecular Weight:480.52
Hs Code.:

Synonyms:

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Chemical Property of 15-O-benzyl-13-deoxy-isatisine A

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Technology Process of 15-O-benzyl-13-deoxy-isatisine A

There total 10 articles about 15-O-benzyl-13-deoxy-isatisine A 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:

Reference yield:

: 1402730-55-5
8-[(tert-butyldimethylsilyloxy)methyl]-2,2-dimethyl-1,3,7-trioxaspiro[4.4]nonan-6-one

: 1402730-62-4
15-O-benzyl-13-deoxy-isatisine A

Guidance literature:: Multi-step reaction with 12 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 1 h / -78 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 0 °C

3.2: 3 h / 0 °C

4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / methanol / 8 h / 0 - 20 °C

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / Reflux

7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 10 h / 20 °C

8.1: methanol; hexane; toluene / 0.33 h / 0 °C

9.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 8 h / 20 °C / Inert atmosphere

10.1: indium(III) chloride / acetonitrile / 5 h / 20 °C / Inert atmosphere

11.1: methanol; lithium hydroxide monohydrate / tetrahydrofuran / 8 h / 20 °C

12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 18 h / Reflux

With methanol; triethylsilane; indium(III) chloride; bis-triphenylphosphine-palladium(II) chloride; dichloro bis(acetonitrile) palladium(II); sodium chlorite; copper(l) iodide; n-butyllithium; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; tert-butyl alcohol; 4.1: Sonogashira coupling;
DOI:10.1002/chem.201103604

Reference yield:

: 1402730-56-6
8-[(tert-butyldimethylsilyloxy)methyl]-2,2-dimethyl-6-[(trimethylsilyl)ethynyl]-1,3,7-trioxaspiro[4.4]nonan-6-ol

: 1402730-62-4
15-O-benzyl-13-deoxy-isatisine A

Guidance literature:: Multi-step reaction with 11 steps

1.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 1 h / -78 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 0 °C

2.2: 3 h / 0 °C

3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / methanol / 8 h / 0 - 20 °C

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / Reflux

6.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 10 h / 20 °C

7.1: methanol; hexane; toluene / 0.33 h / 0 °C

8.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 8 h / 20 °C / Inert atmosphere

9.1: indium(III) chloride / acetonitrile / 5 h / 20 °C / Inert atmosphere

10.1: methanol; lithium hydroxide monohydrate / tetrahydrofuran / 8 h / 20 °C

11.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 18 h / Reflux

With methanol; triethylsilane; indium(III) chloride; bis-triphenylphosphine-palladium(II) chloride; dichloro bis(acetonitrile) palladium(II); sodium chlorite; copper(l) iodide; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; tert-butyl alcohol; 3.1: Sonogashira coupling;
DOI:10.1002/chem.201103604

Reference yield:

: 1402730-54-4
8-(benzyloxymethyl)-6-ethynyl-2,2-dimethyl-1,3,7-trioxaspiro[4.4]nonane

: 1402730-62-4
15-O-benzyl-13-deoxy-isatisine A

Guidance literature:: Multi-step reaction with 9 steps

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2: toluene-4-sulfonic acid / methanol / 8 h / 0 - 20 °C

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / Reflux

4: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 10 h / 20 °C

5: methanol; hexane; toluene / 0.33 h / 0 °C

6: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 8 h / 20 °C / Inert atmosphere

7: indium(III) chloride / acetonitrile / 5 h / 20 °C / Inert atmosphere

8: methanol; lithium hydroxide monohydrate / tetrahydrofuran / 8 h / 20 °C

9: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 18 h / Reflux

With methanol; indium(III) chloride; bis-triphenylphosphine-palladium(II) chloride; dichloro bis(acetonitrile) palladium(II); sodium chlorite; copper(l) iodide; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; lithium hydroxide monohydrate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 1: Sonogashira coupling;
DOI:10.1002/chem.201103604