(1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol

Base Information

Chemical Name:(1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol
CAS No.:1319211-71-6
Molecular Formula:C₂₄H₄₁NO₄Si
Molecular Weight:435.679
Hs Code.:

Synonyms:(1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol

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Chemical Property of (1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol

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Technology Process of (1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol

There total 10 articles about (1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol 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: 99.0%

: 1319211-69-2
(1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1319211-71-6
(1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 19h; regioselective reaction;
DOI:10.1016/j.tet.2011.05.129

Reference yield:

: 1319211-61-4
(Z)-1-phenyl-N-(((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methylene)methanamine N-oxide

: 1319211-71-6
(1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: samarium diiodide; water / tetrahydrofuran / 1 h / -88 - -81 °C / Inert atmosphere

2.1: acetic acid; zinc / tetrahydrofuran; water / 1.5 h / 50 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

3.2: 20 °C / Inert atmosphere

4.1: water; acetic acid / 72 h / 40 °C

4.2: pH > 10

5.1: 1H-imidazole / dichloromethane / 19 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; samarium diiodide; water; acetic acid; zinc; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tet.2011.05.129

Reference yield:

: 1319211-60-3
methyl 4-(benzyl(hydroxy)amino)-4-((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)butanoate

: 1319211-71-6
(1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetic acid; zinc / tetrahydrofuran; water / 1.5 h / 50 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

2.2: 20 °C / Inert atmosphere

3.1: water; acetic acid / 72 h / 40 °C

3.2: pH > 10

4.1: 1H-imidazole / dichloromethane / 19 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; water; acetic acid; zinc; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tet.2011.05.129