2-[5-(benzyloxymethyl)-3-hydroxy-3-(methoxycarbonyl)tetrahydrofuran-2-yl]-3-oxo-3H-indole 1-oxide

Base Information

Chemical Name:2-[5-(benzyloxymethyl)-3-hydroxy-3-(methoxycarbonyl)tetrahydrofuran-2-yl]-3-oxo-3H-indole 1-oxide
CAS No.:1402730-60-2
Molecular Formula:C₂₂H₂₁NO₇
Molecular Weight:411.411
Hs Code.:

Synonyms:2-[5-(benzyloxymethyl)-3-hydroxy-3-(methoxycarbonyl)tetrahydrofuran-2-yl]-3-oxo-3H-indole 1-oxide

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Chemical Property of 2-[5-(benzyloxymethyl)-3-hydroxy-3-(methoxycarbonyl)tetrahydrofuran-2-yl]-3-oxo-3H-indole 1-oxide

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Technology Process of 2-[5-(benzyloxymethyl)-3-hydroxy-3-(methoxycarbonyl)tetrahydrofuran-2-yl]-3-oxo-3H-indole 1-oxide

There total 8 articles about 2-[5-(benzyloxymethyl)-3-hydroxy-3-(methoxycarbonyl)tetrahydrofuran-2-yl]-3-oxo-3H-indole 1-oxide 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: 59.0%

: 1402730-53-3
methyl 5-(benzyloxymethyl)-3-hydroxy-2-[(2-nitrophenyl)ethynyl]tetrahydrofuran-3-carboxylate

: 1402730-60-2
2-[5-(benzyloxymethyl)-3-hydroxy-3-(methoxycarbonyl)tetrahydrofuran-2-yl]-3-oxo-3H-indole 1-oxide

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); In acetonitrile; at 20 ℃; for 8h; Inert atmosphere;
DOI:10.1002/chem.201103604

Reference yield:

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

: 1402730-60-2
2-[5-(benzyloxymethyl)-3-hydroxy-3-(methoxycarbonyl)tetrahydrofuran-2-yl]-3-oxo-3H-indole 1-oxide

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 78687-63-5
2,6-O-isopropylidene-α-D-glucoisosaccharino-1,4-lactone

: 1402730-60-2
2-[5-(benzyloxymethyl)-3-hydroxy-3-(methoxycarbonyl)tetrahydrofuran-2-yl]-3-oxo-3H-indole 1-oxide

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1H-imidazole / dichloromethane / 4 h / 0 °C

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

2.2: 1 h / -78 °C / Inert atmosphere

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

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

4.2: 3 h / 0 °C

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

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

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / Reflux

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

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

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

With 1H-imidazole; triethylsilane; 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; boron trifluoride diethyl etherate; sodium hydride; toluene-4-sulfonic acid; 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; 5.1: Sonogashira coupling;
DOI:10.1002/chem.201103604