methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

Base Information

Chemical Name:methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate
CAS No.:1416081-14-5
Molecular Formula:C₄₀H₄₆N₂O₉S₃Si
Molecular Weight:823.097
Hs Code.:

methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

Synonyms:methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

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Chemical Property of methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

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Technology Process of methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

There total 6 articles about methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-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:

: 35387-59-8
1,2-Bis(phenylsulfonyl)ethylene

: 1416081-13-4
(E)-methyl 2-{[3-(2-[(tert-butyldimethylsilyloxy)ethyl])-1-(phenylsulfonyl)-1H-indol-2-yl]methylene}aminoacetate

: 1416081-14-5
methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

: methyl (2S,3S,4S,5R)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

Guidance literature:: With 1,4-diaza-bicyclo[2.2.2]octane; silver trifluoroacetate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In toluene; at 25 ℃; for 48h; Overall yield = 60 %; Darkness;
DOI:10.1016/j.tetasy.2012.10.015

Reference yield:

: 101079-48-5
3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole

: 1416081-14-5
methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

: methyl (2S,3S,4S,5R)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 25 °C / Darkness

1.2: 19 h / 25 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Darkness

2.2: -78 - 25 °C / Darkness

3.1: triethylamine; magnesium sulfate / chloroform / 16 h / Darkness; Reflux

4.1: silver trifluoroacetate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); 1,4-diaza-bicyclo[2.2.2]octane / toluene / 48 h / 25 °C / Darkness

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; silver trifluoroacetate; sodium hydride; magnesium sulfate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; In tetrahydrofuran; hexane; chloroform; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1016/j.tetasy.2012.10.015

Reference yield:

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

: 1416081-14-5
methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

: methyl (2S,3S,4S,5R)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H-indol-2-yl}-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Darkness

1.2: -78 - 25 °C / Darkness

2.1: triethylamine; magnesium sulfate / chloroform / 16 h / Darkness; Reflux

3.1: silver trifluoroacetate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); 1,4-diaza-bicyclo[2.2.2]octane / toluene / 48 h / 25 °C / Darkness

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; silver trifluoroacetate; magnesium sulfate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; In tetrahydrofuran; hexane; chloroform; toluene;
DOI:10.1016/j.tetasy.2012.10.015