(2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine

Base Information

Chemical Name:(2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine
CAS No.:916588-58-4
Molecular Formula:C₂₇H₄₁NO₄SSi
Molecular Weight:503.778
Hs Code.:

Synonyms:(2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine

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Chemical Property of (2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine

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Technology Process of (2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine

There total 3 articles about (2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine 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%

: 916588-52-8
2-(1-hydroxypropyl)-4-[(tert-butyldimethylsilanyl)oxy]-1-[(4-methylphenyl)sulfonyl]pyrrolidine

: 100-39-0
benzyl bromide

: 916588-58-4
(2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃; for 20h;
DOI:10.1016/j.tet.2006.09.004

Reference yield:

: 863396-18-3
(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde

: 916588-58-4
(2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1: 372 mg / tetrahydrofuran / -78 - 20 °C

2: 86 percent / sodium hydride / tetrahydrofuran / 20 h / 20 °C

With sodium hydride; In tetrahydrofuran; 1: Grignard addition;
DOI:10.1016/j.tet.2006.09.004

Reference yield:

: 261157-02-2
(2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine

: 916588-58-4
(2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

2: 372 mg / tetrahydrofuran / -78 - 20 °C

3: 86 percent / sodium hydride / tetrahydrofuran / 20 h / 20 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxydation / 2: Grignard addition;
DOI:10.1016/j.tet.2006.09.004