[(1R),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-1-(tert-butyldimethylsilyl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate

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Chemical Name:[(1R),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-1-(tert-butyldimethylsilyl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate
CAS No.:909806-25-3
Molecular Formula:C₂₆H₄₄N₂O₂SSi
Molecular Weight:476.799
Hs Code.:

Synonyms:[(1R),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-1-(tert-butyldimethylsilyl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate

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Chemical Property of [(1R),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-1-(tert-butyldimethylsilyl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate

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Technology Process of [(1R),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-1-(tert-butyldimethylsilyl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate

There total 5 articles about [(1R),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-1-(tert-butyldimethylsilyl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate 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: 65.0%

: 909806-18-4
(S)-S-[(1-benzylpyrrolidin-2-yl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate

: 69739-34-0
t-butyldimethylsiyl triflate

: 909806-25-3
[(1R),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-1-(tert-butyldimethylsilyl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate

Guidance literature:: (S)-S-[(1-benzylpyrrolidin-2-yl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In toluene; at -78 ℃; for 3h;

t-butyldimethylsiyl triflate; In toluene; Further stages.;
DOI:10.1002/chem.200601853

Reference yield:

: 262428-27-3
(S)-S-[(1-benzylpyrrolidin-2-yl)methyl] ethanethioate

: 909806-25-3
[(1R),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-1-(tert-butyldimethylsilyl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium aluminium hydride / diethyl ether / 1.5 h / 0 - 20 °C

2.1: 5.5 g / NaH / tetrahydrofuran; various solvent(s) / 24 h / 20 °C

3.1: N,N,N',N'-tetramethylethylenediamine; sBuLi / toluene / 3 h / -78 °C

3.2: 65 percent / toluene

With lithium aluminium tetrahydride; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; sodium hydride; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1002/chem.200601853

Reference yield:

: 909806-22-0
[(1S),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-deuteriomethyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate

: 909806-25-3
[(1R),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-1-(tert-butyldimethylsilyl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate

Guidance literature:: Multi-step reaction with 2 steps

1.1: N,N,N',N'-tetramethylethylenediamine; sBuLi / toluene / 3 h / -78 °C

1.2: MeOD / toluene / 0.25 h

2.1: N,N,N',N'-tetramethylethylenediamine; sBuLi / toluene / 3 h / -78 °C

2.2: 65 percent / toluene

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In toluene;
DOI:10.1002/chem.200601853