(2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine

Base Information

Chemical Name:(2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine
CAS No.:1420298-18-5
Molecular Formula:C₂₅H₃₁NO₄
Molecular Weight:409.525
Hs Code.:

Synonyms:(2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine

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Chemical Property of (2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine

Chemical Property:

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Technology Process of (2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine

There total 13 articles about (2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine 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: 78.0%

: 1420298-19-6
(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutoxycarbonylamino)-1-pivaloylhex-2-ene

: 1420298-18-5
(2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; at 20 ℃; for 4h; Cooling with ice;
DOI:10.5012/bkcs.2012.33.11.3554

Reference yield: 72.0%

: tert-butyl ((2S,3S,4S)-2,3-bis(benzyloxy)-4-hydroxyhex-5-en-1-yl)carbamate

: 1420298-18-5
(2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine

Guidance literature:: With C₄₉H₄₉O₈P₂Pd⁽¹⁺⁾*CF₃O₃S^(1-); In toluene; at 40 ℃; for 45h;
DOI:10.1002/chem.201705164

Reference yield:

: 1420298-21-0
(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)hex-2-en-1-ol

: 1420298-18-5
(2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: dmap / dichloromethane / 4 h / 0 - 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C

3: triphenylphosphine; di-isopropyl azodicarboxylate; diphenylphosphoranyl azide / tetrahydrofuran / 2 h / 0 - 20 °C

4: triphenylphosphine / tetrahydrofuran / 1 h / Reflux

5: triethylamine / dichloromethane / 4 h / 0 - 20 °C

6: diisobutylaluminium hydride / dichloromethane; toluene / 0.42 h / -78 °C

7: dichloro bis(acetonitrile) palladium(II) / tetrahydrofuran / 4 h / 20 °C / Cooling with ice

With dmap; dichloro bis(acetonitrile) palladium(II); di-isopropyl azodicarboxylate; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; 4: |Staudinger Azide Reduction;
DOI:10.5012/bkcs.2012.33.11.3554