(2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-(2,2,2-trifluoroacetimidoyloxy)pent-1-enyl]-N-(tert-butoxycarbonyl)pyrrolidine

Base Information

Chemical Name:(2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-(2,2,2-trifluoroacetimidoyloxy)pent-1-enyl]-N-(tert-butoxycarbonyl)pyrrolidine
CAS No.:260978-70-9
Molecular Formula:C₂₄H₃₃F₃N₂O₅
Molecular Weight:486.532
Hs Code.:

Synonyms:(2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-(2,2,2-trifluoroacetimidoyloxy)pent-1-enyl]-N-(tert-butoxycarbonyl)pyrrolidine

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Chemical Property of (2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-(2,2,2-trifluoroacetimidoyloxy)pent-1-enyl]-N-(tert-butoxycarbonyl)pyrrolidine

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Technology Process of (2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-(2,2,2-trifluoroacetimidoyloxy)pent-1-enyl]-N-(tert-butoxycarbonyl)pyrrolidine

There total 4 articles about (2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-(2,2,2-trifluoroacetimidoyloxy)pent-1-enyl]-N-(tert-butoxycarbonyl)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: 45.0%

: 353-85-5
trifluoroacetonitrile

: 260978-68-5
(2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-hydroxypent-1-enyl]-N-(tert-butoxycarbonyl)pyrrolidine

: 260978-70-9
(2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-(2,2,2-trifluoroacetimidoyloxy)pent-1-enyl]-N-(tert-butoxycarbonyl)pyrrolidine

Guidance literature:: (2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-hydroxypent-1-enyl]-N-(tert-butoxycarbonyl)pyrrolidine; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.25h;

trifluoroacetonitrile; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1039/a905772b

Reference yield:

: 63296-55-9
(S)-(-) ethyl 2-<(benzyloxy)ymethoxy>propanoate

: 260978-70-9
(2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-(2,2,2-trifluoroacetimidoyloxy)pent-1-enyl]-N-(tert-butoxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 90 percent / tetrahydrofuran; hexane / 2 h / -78 °C

2.1: 76 percent / LiCl; DBU / acetonitrile / 20 h

3.1: 89 percent / Zn(BH₄)2 / diethyl ether / 2.5 h / -35 °C

4.1: BuLi / tetrahydrofuran / 0.25 h / 0 °C

4.2: 45 percent / tetrahydrofuran / 1 h / -78 °C

With n-butyllithium; zinc(II) tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; acetonitrile; 1.1: Metallation / 1.2: Acylation / 2.1: Condensation / 3.1: Reduction / 4.1: Metallation / 4.2: Addition;
DOI:10.1039/a905772b

Reference yield:

: 96823-34-6
Dimethyl [(3S)-3-benzyloxymethoxy-2-oxobutyl]phosphonate

: 260978-70-9
(2S)-2-[(3R,4S,1E)-4-Benzyloxymethoxy-3-(2,2,2-trifluoroacetimidoyloxy)pent-1-enyl]-N-(tert-butoxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 76 percent / LiCl; DBU / acetonitrile / 20 h

2.1: 89 percent / Zn(BH₄)2 / diethyl ether / 2.5 h / -35 °C

3.1: BuLi / tetrahydrofuran / 0.25 h / 0 °C

3.2: 45 percent / tetrahydrofuran / 1 h / -78 °C

With n-butyllithium; zinc(II) tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; diethyl ether; acetonitrile; 1.1: Condensation / 2.1: Reduction / 3.1: Metallation / 3.2: Addition;
DOI:10.1039/a905772b