methyl (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-((R)-3-oxo-2-(1-tosyl-1H-indol-3-yl)indolin-2-yl)tetrahydrofuran-3-carboxylate

Base Information

Chemical Name:methyl (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-((R)-3-oxo-2-(1-tosyl-1H-indol-3-yl)indolin-2-yl)tetrahydrofuran-3-carboxylate
CAS No.:1362063-16-8
Molecular Formula:C₃₀H₂₈N₂O₉S
Molecular Weight:592.626
Hs Code.:

Synonyms:methyl (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-((R)-3-oxo-2-(1-tosyl-1H-indol-3-yl)indolin-2-yl)tetrahydrofuran-3-carboxylate

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Chemical Property of methyl (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-((R)-3-oxo-2-(1-tosyl-1H-indol-3-yl)indolin-2-yl)tetrahydrofuran-3-carboxylate

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Technology Process of methyl (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-((R)-3-oxo-2-(1-tosyl-1H-indol-3-yl)indolin-2-yl)tetrahydrofuran-3-carboxylate

There total 7 articles about methyl (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-((R)-3-oxo-2-(1-tosyl-1H-indol-3-yl)indolin-2-yl)tetrahydrofuran-3-carboxylate 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: 62.0%

: 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

: 1362063-16-8
methyl (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-((R)-3-oxo-2-(1-tosyl-1H-indol-3-yl)indolin-2-yl)tetrahydrofuran-3-carboxylate

Guidance literature:: (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; With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; at 20 ℃; for 4h;

With copper(l) chloride; In methanol; dichloromethane; for 6h; Reflux;
DOI:10.1016/j.tet.2014.09.028

Reference yield:

: 1334368-26-1
1'-tosyl-1'H,3H-2,3'-biindol-3-one

: 1362063-16-8
methyl (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-((R)-3-oxo-2-(1-tosyl-1H-indol-3-yl)indolin-2-yl)tetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 4 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

3.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen / methanol / 4 h / 20 °C

4.1: copper(l) chloride / dichloromethane / 6 h / Reflux

With hydrogenchloride; 20 wt.% Pd(OH)2 on activated carbon; hydrogen; copper(l) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/ol300379g

Reference yield:

: 1362063-12-4
(4aR,8R,8aS)-8-((benzyloxy)methoxy)-2,2-dimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine

: 1362063-16-8
methyl (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-((R)-3-oxo-2-(1-tosyl-1H-indol-3-yl)indolin-2-yl)tetrahydrofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: 1 h

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

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

3.2: 3.5 h / -78 - 20 °C / Inert atmosphere

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

5.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen / methanol / 4 h / 20 °C

6.1: copper(l) chloride / dichloromethane / 6 h / Reflux

With hydrogenchloride; dimethylsulfide borane complex; 20 wt.% Pd(OH)2 on activated carbon; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; copper(l) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Hydroboration reaction;
DOI:10.1021/ol300379g