(S)-2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(1H-indol-3-yl)indolin-3-one

Base Information

Chemical Name:(S)-2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(1H-indol-3-yl)indolin-3-one
CAS No.:1413282-09-3
Molecular Formula:C₃₂H₃₂N₂O₆
Molecular Weight:540.616
Hs Code.:

Synonyms:(S)-2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(1H-indol-3-yl)indolin-3-one

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Chemical Property of (S)-2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(1H-indol-3-yl)indolin-3-one

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Technology Process of (S)-2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(1H-indol-3-yl)indolin-3-one

There total 7 articles about (S)-2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(1H-indol-3-yl)indolin-3-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:

Reference yield: 65.0%

: 120-72-9
indole

: 1413282-20-8
2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(acetoxymethyl)-2,2-dimethyltetrahydrofuro-[3,4-d][1,3]dioxol-4-yl)-3-oxo-3H-indole 1-oxide

: 1413282-09-3
(S)-2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(1H-indol-3-yl)indolin-3-one

Guidance literature:: indole; 2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(acetoxymethyl)-2,2-dimethyltetrahydrofuro-[3,4-d][1,3]dioxol-4-yl)-3-oxo-3H-indole 1-oxide; With indium(III) chloride; In acetonitrile; at 60 ℃; for 12h; Inert atmosphere;

With potassium carbonate; In methanol; at 20 ℃; for 0.5h;
DOI:10.1021/jo302198v

Reference yield:

: 1413282-23-1
((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

: 1413282-09-3
(S)-2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(1H-indol-3-yl)indolin-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine; triethylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

2.1: pyridine; dmap / 2 h / 20 °C

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

4.1: indium(III) chloride / acetonitrile / 12 h / 60 °C / Inert atmosphere

4.2: 0.5 h / 20 °C

With pyridine; dmap; indium(III) chloride; bis-triphenylphosphine-palladium(II) chloride; dichloro bis(acetonitrile) palladium(II); copper(l) iodide; triethylamine; triphenylphosphine; In tetrahydrofuran; acetonitrile; 1.1: |Sonogashira Cross-Coupling;
DOI:10.1021/jo302198v

Reference yield:

: 1413282-18-4
((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

: 1413282-09-3
(S)-2-((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(1H-indol-3-yl)indolin-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine; dmap / 2 h / 20 °C

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

3.1: indium(III) chloride / acetonitrile / 12 h / 60 °C / Inert atmosphere

3.2: 0.5 h / 20 °C

With pyridine; dmap; indium(III) chloride; dichloro bis(acetonitrile) palladium(II); In acetonitrile;
DOI:10.1021/jo302198v