2-{1-benzenesulfonyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-indol-2-yl}-2-hydroxy-propionic acid methyl ester

Base Information

Chemical Name:2-{1-benzenesulfonyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-indol-2-yl}-2-hydroxy-propionic acid methyl ester
CAS No.:140920-83-8
Molecular Formula:C₂₆H₃₅NO₆SSi
Molecular Weight:517.719
Hs Code.:

2-{1-benzenesulfonyl-3-[2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-ethyl]-1<i>H</i>-indol-2-yl}-2-hydroxy-propionic acid methyl ester

Synonyms:2-{1-benzenesulfonyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-indol-2-yl}-2-hydroxy-propionic acid methyl ester

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Chemical Property of 2-{1-benzenesulfonyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-indol-2-yl}-2-hydroxy-propionic acid methyl ester

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Technology Process of 2-{1-benzenesulfonyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-indol-2-yl}-2-hydroxy-propionic acid methyl ester

There total 1 articles about 2-{1-benzenesulfonyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-indol-2-yl}-2-hydroxy-propionic acid methyl ester 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: 63.0%

: 600-22-6
pyruvic acid methyl ester

: 140920-82-7
1-(O-tert-butyldimethylsilyl)-2-<3-(1-phenylsulfonyl)indolyl>ethanol

: 140920-83-8
2-{1-benzenesulfonyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-indol-2-yl}-2-hydroxy-propionic acid methyl ester

Guidance literature:: 1-(O-tert-butyldimethylsilyl)-2-<3-(1-phenylsulfonyl)indolyl>ethanol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃;

pyruvic acid methyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1021/jo047834a

Reference yield:

: 140920-83-8
2-{1-benzenesulfonyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-indol-2-yl}-2-hydroxy-propionic acid methyl ester

: 2-[1-benzenesulfonyl-3-(2-hydroxy-ethyl)-1H-indol-2-yl]-2-hydroxy-propionic acid methyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo047834a

Reference yield:

: 140920-83-8
2-{1-benzenesulfonyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-indol-2-yl}-2-hydroxy-propionic acid methyl ester

: C₃₂H₃₂N₂O₉S

Guidance literature:: Multi-step reaction with 6 steps

1.1: BF₃*OEt₂ / CH₂Cl₂ / 2 h / 20 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 0.17 h / 0 °C

3.1: p-TsOH*H₂O / benzene / 1 h / Heating

4.1: 1.4 g / Na₂CO₃ / methanol; H₂O / 0.5 h / Heating

5.1: Jones' reagent / acetone / 2 h / 20 °C

5.2: PCl₅ / diethyl ether / 2 h / 20 °C

5.3: 62 percent / tetrahydrofuran / 20 h

6.1: 91 percent / Rh₂(OAc)4 / benzene / 2 h / 90 °C / microwave irradiation

With dmap; jones' reagent; boron trifluoride diethyl etherate; sodium carbonate; toluene-4-sulfonic acid; triethylamine; dirhodium tetraacetate; In methanol; dichloromethane; water; acetone; benzene; 5.1: Jones' oxidation / 6.1: intramolecular Diels-Alder cycloaddition;
DOI:10.1021/jo047834a