Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester

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Chemical Name:Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester
CAS No.:794518-68-6
Molecular Formula:C₃₁H₅₂N₂O₃SSi
Molecular Weight:560.917
Hs Code.:

Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester

Synonyms:Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester

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Chemical Property of Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester

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Technology Process of Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester

There total 14 articles about Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester 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:

: 624-92-0
Dimethyldisulphide

: 794518-67-5
[2R,3S,3(1Z),4S]-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-[2-(N,N-diisopropylcarbamoyloxy)ethenyl]-4-(1-methylethenyl)pyrrolidine

: 794518-68-6
Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester

Guidance literature:: [2R,3S,3(1Z),4S]-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-[2-(N,N-diisopropylcarbamoyloxy)ethenyl]-4-(1-methylethenyl)pyrrolidine; With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 1h;

Dimethyldisulphide; In tetrahydrofuran; pentane; at -78 - 20 ℃;
DOI:10.1021/ol0485666

Reference yield:

: 19009-39-3
N,N-diisopropylcarbamoyl chloride

: 794518-68-6
Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 53 percent / tetrahydrofuran / 12 h / 70 °C

2.1: (-)-sparteine; nBuLi / toluene; hexane / 1.5 h / -78 °C

3.1: TMEDA; tBuLi / tetrahydrofuran; pentane / 1 h / -78 °C

3.2: tetrahydrofuran; pentane / -78 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; sodium hydride; (-)-sparteine; In tetrahydrofuran; hexane; toluene; pentane;
DOI:10.1002/ejoc.200400824

Reference yield:

: 123639-56-5,131110-76-4,144001-42-3
methyl (2R)-2-(benzylamino)-3-hydroxypropanoate

: 794518-68-6
Diisopropyl-carbamic acid (E)-2-[(2S,3R,4S)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-isopropenyl-pyrrolidin-3-yl]-1-methylsulfanyl-vinyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 90 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

2.1: 47 percent / LiBH₄ / tetrahydrofuran; toluene / 0.33 h / 100 °C

3.1: NaHCO₃ / acetonitrile / 0.5 h / 20 °C

3.2: 82 percent / acetonitrile / 3 h / Heating

4.1: (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -78 °C

4.2: 75 percent / CH₂Cl₂ / 3 h / 25 °C

5.1: 81 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

6.1: MsCl; Et₃N / CH₂Cl₂ / 1 h / -40 °C

6.2: 71 percent / LiCl / tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

7.1: 70 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -78 °C

8.1: NaH / tetrahydrofuran / 1 h / 20 °C

8.2: 53 percent / tetrahydrofuran / 12 h / 70 °C

9.1: (-)-sparteine; nBuLi / toluene; hexane / 1.5 h / -78 °C

10.1: TMEDA; tBuLi / tetrahydrofuran; pentane / 1 h / -78 °C

10.2: tetrahydrofuran; pentane / -78 °C

With dmap; lithium borohydride; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; (-)-sparteine; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile; pentane; 4.1: Swern oxidation;
DOI:10.1002/ejoc.200400824