(2S,3R,4R,4'S)-1-benzyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-hydroxy-3-[2-(trimethylsilyl)ethoxy]pyrrolidine

Base Information

Chemical Name:(2S,3R,4R,4'S)-1-benzyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-hydroxy-3-[2-(trimethylsilyl)ethoxy]pyrrolidine
CAS No.:1312678-24-2
Molecular Formula:C₂₁H₃₅NO₄Si
Molecular Weight:393.599
Hs Code.:

Synonyms:(2S,3R,4R,4'S)-1-benzyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-hydroxy-3-[2-(trimethylsilyl)ethoxy]pyrrolidine

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Chemical Property of (2S,3R,4R,4'S)-1-benzyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-hydroxy-3-[2-(trimethylsilyl)ethoxy]pyrrolidine

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Technology Process of (2S,3R,4R,4'S)-1-benzyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-hydroxy-3-[2-(trimethylsilyl)ethoxy]pyrrolidine

There total 4 articles about (2S,3R,4R,4'S)-1-benzyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-hydroxy-3-[2-(trimethylsilyl)ethoxy]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%

: (2S,3R,4R,4'S)-1-benzyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3-[2-(trimethylsilyl)ethoxy]-4-(methylsulfonyloxy)pyrrolidine

: 1312678-24-2
(2S,3R,4R,4'S)-1-benzyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-hydroxy-3-[2-(trimethylsilyl)ethoxy]pyrrolidine

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; hexanes; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201100230

Reference yield:

: 444307-95-3
(3S,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-[2-(trimethylsilyl)ethoxy]-3,6-dihydro-2H-1,2-oxazine

: 1312678-24-2
(2S,3R,4R,4'S)-1-benzyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-hydroxy-3-[2-(trimethylsilyl)ethoxy]pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: borane-THF / tetrahydrofuran / -30 - 20 °C / Inert atmosphere

1.2: -10 - 20 °C / Inert atmosphere

2.1: samarium diiodide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere

4.1: lithium diisopropyl amide / tetrahydrofuran; hexanes / -78 - 20 °C / Inert atmosphere

With samarium diiodide; borane-THF; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexanes; dichloromethane; 1.1: Hydroboration reaction;
DOI:10.1002/ejoc.201100230

Reference yield:

: (4S,1'R,2'R,3'R)-4-[1'-benzylamino-3',4'-dihydroxy-2'-[(2-trimethylsilyl)ethoxy]-but-1'-yl]-2,2-dimethyl-1,3-dioxolane

: 1312678-24-2
(2S,3R,4R,4'S)-1-benzyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-hydroxy-3-[2-(trimethylsilyl)ethoxy]pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere

2: lithium diisopropyl amide / tetrahydrofuran; hexanes / -78 - 20 °C / Inert atmosphere

With triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexanes; dichloromethane;
DOI:10.1002/ejoc.201100230