(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.:1267579-95-2
Molecular Formula:C₃₀H₄₅NO₃S₂Si
Molecular Weight:559.91
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: 47.0%

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

: 106-45-6
para-thiocresol

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

Guidance literature:: With indium(III) chloride; In dichloromethane; for 24h; Reflux;
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

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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

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

Guidance literature:: Multi-step reaction with 4 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

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