(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(3-[1,3]dioxolan-2-yl-propyl)-1-(toluene-4-sulfonyl)-pyrrolidine

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Chemical Name:(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(3-[1,3]dioxolan-2-yl-propyl)-1-(toluene-4-sulfonyl)-pyrrolidine
CAS No.:866141-92-6
Molecular Formula:C₂₃H₃₉NO₅SSi
Molecular Weight:469.718
Hs Code.:

Synonyms:(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(3-[1,3]dioxolan-2-yl-propyl)-1-(toluene-4-sulfonyl)-pyrrolidine

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Chemical Property of (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(3-[1,3]dioxolan-2-yl-propyl)-1-(toluene-4-sulfonyl)-pyrrolidine

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Technology Process of (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(3-[1,3]dioxolan-2-yl-propyl)-1-(toluene-4-sulfonyl)-pyrrolidine

There total 8 articles about (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(3-[1,3]dioxolan-2-yl-propyl)-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: 90.0%

: 866141-89-1
(2S,4R)-4-t-butyldimethylsilyloxy-2-[3-(1,3-dioxolan-2-yl)prop-1-en-1-yl]-1-(4-methylphenylsulfonyl)pyrrolidine

: 866141-92-6
(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(3-[1,3]dioxolan-2-yl-propyl)-1-(toluene-4-sulfonyl)-pyrrolidine

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 10h;
DOI:10.3987/COM-05-10470

Reference yield:

: 1063998-64-0
(2S,4R)-4-Hydroxy-pyrrolidine-2-carbonyl chloride

: 866141-92-6
(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(3-[1,3]dioxolan-2-yl-propyl)-1-(toluene-4-sulfonyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / CH₂Cl₂

2.1: imidazole / dimethylformamide

3.1: sodium borohydride; lithium chloride / methanol

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

4.2: 75 percent / n-butyllithium / tetrahydrofuran; hexane / -78 - 8 °C

5.1: 90 percent / H₂ / Pd/C / ethyl acetate / 10 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; triethylamine; N,N-dimethyl-formamide; 4.1: Swern oxidation;
DOI:10.3987/COM-05-10470

Reference yield:

: (2S,4R)-4-Hydroxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbonyl chloride

: 866141-92-6
(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(3-[1,3]dioxolan-2-yl-propyl)-1-(toluene-4-sulfonyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: imidazole / dimethylformamide

2.1: sodium borohydride; lithium chloride / methanol

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

3.2: 75 percent / n-butyllithium / tetrahydrofuran; hexane / -78 - 8 °C

4.1: 90 percent / H₂ / Pd/C / ethyl acetate / 10 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; hydrogen; dimethyl sulfoxide; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; triethylamine; N,N-dimethyl-formamide; 3.1: Swern oxidation;
DOI:10.3987/COM-05-10470