(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
• Mol file: 1420298-18-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutoxycarbonylamino)-1-pivaloylhex-2-ene (1420298-19-6) → (2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine (1420298-18-5)

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

Guidance literature:

With C₄₉H₄₉O₈P₂Pd⁽¹⁺⁾*CF₃O₃S^(1-); In toluene; at 40 ℃; for 45h;

DOI:10.1002/chem.201705164

Reference yield:

(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)hex-2-en-1-ol (1420298-21-0) → (2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine (1420298-18-5)

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

upstream raw materials:

(2R,3S)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal

(2S,3S)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol

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

(4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene

Downstream raw materials:

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

(+)-lentiginosine

Refernces

• 1、 Sadhu, Partha Sarathi,Santhoshi, Amlipur,Rao, Vaidya Jayathirtha. "Total synthesis of azasugar 1,4-Dideoxy-1,4-imino-D-galacitol". . p. 3554 - 3558. Retrieved 2013/01/16.