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

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Chemical Name:[2R,3S,3(1Z),4S]-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-[2-(N,N-diisopropylcarbamoyloxy)ethenyl]-4-(1-methylethenyl)pyrrolidine
CAS No.:794518-67-5
Molecular Formula:C₃₀H₅₀N₂O₃Si
Molecular Weight:514.824
Hs Code.:

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

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Chemical Property of [2R,3S,3(1Z),4S]-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-[2-(N,N-diisopropylcarbamoyloxy)ethenyl]-4-(1-methylethenyl)pyrrolidine

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Technology Process of [2R,3S,3(1Z),4S]-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-[2-(N,N-diisopropylcarbamoyloxy)ethenyl]-4-(1-methylethenyl)pyrrolidine

There total 14 articles about [2R,3S,3(1Z),4S]-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-[2-(N,N-diisopropylcarbamoyloxy)ethenyl]-4-(1-methylethenyl)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:

: 794518-66-4
(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-yl N,N-diisopropylcarbamate

: 794518-71-1
[2R,3R,3(1Z),4R]-1-benzyl-2-[(tert-butyldimethylsilyloxy)methyl]-3-[2-(N,N-diisopropylcarbamoyloxy)ethenyl]-4-(1-methylethenyl)pyrrolidine

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

Guidance literature:: With n-butyllithium; (-)-sparteine; In hexane; toluene; at -78 ℃; for 1.5h;
DOI:10.1021/ol0485666

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; sodium hydride; (-)-sparteine; In tetrahydrofuran; hexane; toluene;
DOI:10.1002/ejoc.200400824

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

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

Guidance literature:: Multi-step reaction with 9 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

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