(2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate

Base Information

Chemical Name:(2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate
CAS No.:1267579-99-6
Molecular Formula:C₂₄H₃₁NO₃S₂
Molecular Weight:445.647
Hs Code.:

Synonyms:(2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate

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Chemical Property of (2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate

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Technology Process of (2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate

There total 5 articles about (2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-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: 86.0%

: 1267579-95-2
(2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate

: 1267579-99-6
(2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.333333h;
DOI:10.1002/ejoc.201001211

Reference yield:

: 401564-17-8
(2S,4S)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid

: 1267579-99-6
(2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: indium(III) chloride / dichloromethane / 24 h / Reflux

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

With indium(III) chloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201001211

Reference yield:

: 74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9
(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

: 1267579-99-6
(2S, 4S)-tert-butyl 2-(bis(p-tolylthio)methyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere

2.1: methanol; sodium tetrahydroborate / tetrahydrofuran / 20 °C / Cooling with ice; Inert atmosphere

3.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1.5 h / -78 °C / Inert atmosphere

3.2: 1.5 h / Inert atmosphere

4.1: indium(III) chloride / dichloromethane / 24 h / Reflux

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

With methanol; indium(III) chloride; sodium tetrahydroborate; oxalyl dichloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1002/ejoc.201001211