(2R,4S)-1-(tert-butoxycarbonyl)-2-benzyloxycarbonyl-4-(tert-butyldimethylsiloxy)methylpyrrolidine

Base Information

Chemical Name:(2R,4S)-1-(tert-butoxycarbonyl)-2-benzyloxycarbonyl-4-(tert-butyldimethylsiloxy)methylpyrrolidine
CAS No.:857478-26-3
Molecular Formula:C₂₄H₃₉NO₅Si
Molecular Weight:449.663
Hs Code.:

Synonyms:(2R,4S)-1-(tert-butoxycarbonyl)-2-benzyloxycarbonyl-4-(tert-butyldimethylsiloxy)methylpyrrolidine

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Chemical Property of (2R,4S)-1-(tert-butoxycarbonyl)-2-benzyloxycarbonyl-4-(tert-butyldimethylsiloxy)methylpyrrolidine

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Technology Process of (2R,4S)-1-(tert-butoxycarbonyl)-2-benzyloxycarbonyl-4-(tert-butyldimethylsiloxy)methylpyrrolidine

There total 3 articles about (2R,4S)-1-(tert-butoxycarbonyl)-2-benzyloxycarbonyl-4-(tert-butyldimethylsiloxy)methylpyrrolidine 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: 95.0%

: 857478-22-9
(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)methyl-5-benzyloxycarbonyl-pyrrolidin-2-one

: 857478-26-3
(2R,4S)-1-(tert-butoxycarbonyl)-2-benzyloxycarbonyl-4-(tert-butyldimethylsiloxy)methylpyrrolidine

Guidance literature:: (3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)methyl-5-benzyloxycarbonyl-pyrrolidin-2-one; With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1021/ol050991r

Reference yield:

: 4-hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

: 857478-26-3
(2R,4S)-1-(tert-butoxycarbonyl)-2-benzyloxycarbonyl-4-(tert-butyldimethylsiloxy)methylpyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 53 percent / imidazole / dimethylformamide / 6 h / 20 °C

2.1: DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

2.2: 95 percent / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 °C

With 1H-imidazole; diisobutylaluminium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol050991r

Reference yield:

: 400626-71-3
2-benzyl 1-(tert-butyl) (R)-5-oxopyrrolidine-1,2-dicarboxylate

: 857478-26-3
(2R,4S)-1-(tert-butoxycarbonyl)-2-benzyloxycarbonyl-4-(tert-butyldimethylsiloxy)methylpyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 3 h / -78 °C

1.2: 58 percent / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 53 percent / imidazole / dimethylformamide / 6 h / 20 °C

3.1: DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: 95 percent / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 °C

With 1H-imidazole; titanium tetrachloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol050991r