(S)-2-((2S,4S,5R,6R)-4-((benzyloxy)methoxy)-5-hydroxy-6-(hydroxymethyl)-3-oxotetrahydro-2H-pyran-2-yl)-2-(1-tosyl-1H-indol-3-yl)indolin-3-one

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Chemical Name:(S)-2-((2S,4S,5R,6R)-4-((benzyloxy)methoxy)-5-hydroxy-6-(hydroxymethyl)-3-oxotetrahydro-2H-pyran-2-yl)-2-(1-tosyl-1H-indol-3-yl)indolin-3-one
CAS No.:1362063-14-6
Molecular Formula:C₃₇H₃₄N₂O₉S
Molecular Weight:682.751
Hs Code.:

Synonyms:(S)-2-((2S,4S,5R,6R)-4-((benzyloxy)methoxy)-5-hydroxy-6-(hydroxymethyl)-3-oxotetrahydro-2H-pyran-2-yl)-2-(1-tosyl-1H-indol-3-yl)indolin-3-one

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Chemical Property of (S)-2-((2S,4S,5R,6R)-4-((benzyloxy)methoxy)-5-hydroxy-6-(hydroxymethyl)-3-oxotetrahydro-2H-pyran-2-yl)-2-(1-tosyl-1H-indol-3-yl)indolin-3-one

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Technology Process of (S)-2-((2S,4S,5R,6R)-4-((benzyloxy)methoxy)-5-hydroxy-6-(hydroxymethyl)-3-oxotetrahydro-2H-pyran-2-yl)-2-(1-tosyl-1H-indol-3-yl)indolin-3-one

There total 7 articles about (S)-2-((2S,4S,5R,6R)-4-((benzyloxy)methoxy)-5-hydroxy-6-(hydroxymethyl)-3-oxotetrahydro-2H-pyran-2-yl)-2-(1-tosyl-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: 54.0%

: 1362063-06-6
2-((4aR,6S,8S,8aR)-8-((benzyloxy)methoxy)-2,2-dimethyl-7-oxohexahydropyrano[3,2-d][1,3]dioxin-6-yl)-2-(1-tosyl-1H-indol-3-yl)indolin-3-one

: 1362063-22-6
(R)-2-((2S,4S,5R,6R)-4-((benzyloxy)methoxy)-5-hydroxy-6-(hydroxymethyl)-3-oxotetrahydro-2H-pyran-2-yl)-2-(1-tosyl-1H-indol-3-yl)indolin-3-one

: 1362063-14-6
(S)-2-((2S,4S,5R,6R)-4-((benzyloxy)methoxy)-5-hydroxy-6-(hydroxymethyl)-3-oxotetrahydro-2H-pyran-2-yl)-2-(1-tosyl-1H-indol-3-yl)indolin-3-one

Guidance literature:: With hydrogenchloride; In methanol; water; at 20 ℃; for 2h; optical yield given as %de;
DOI:10.1021/ol300379g

Reference yield:

: 51450-36-3
4,6-O-isopropylidene-D-glucal

: 1362063-14-6
(S)-2-((2S,4S,5R,6R)-4-((benzyloxy)methoxy)-5-hydroxy-6-(hydroxymethyl)-3-oxotetrahydro-2H-pyran-2-yl)-2-(1-tosyl-1H-indol-3-yl)indolin-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

2.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere; Cooling with ice

2.2: 1 h

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 3.5 h / -78 - 20 °C / Inert atmosphere

5.1: hydrogenchloride / methanol; water / 2 h / 20 °C

With hydrogenchloride; dimethylsulfide borane complex; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; 2.1: Hydroboration reaction;
DOI:10.1021/ol300379g

Reference yield:

: 1362063-09-9
(4aR,8S,8aR)-8-((benzyloxy)methoxy)-2,2-dimethyltetrahydropyrano[3,2-d][1,3]dioxin-7(6H)-one

: 1362063-14-6
(S)-2-((2S,4S,5R,6R)-4-((benzyloxy)methoxy)-5-hydroxy-6-(hydroxymethyl)-3-oxotetrahydro-2H-pyran-2-yl)-2-(1-tosyl-1H-indol-3-yl)indolin-3-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 3.5 h / -78 - 20 °C / Inert atmosphere

2.1: hydrogenchloride / methanol; water / 2 h / 20 °C

With hydrogenchloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; water;
DOI:10.1021/ol300379g