ethyl (5-(tert-butyldimethylsilanyloxy)-4-phenylselanyl)-(E)-pent-2-enoate

Base Information

• Chemical Name: ethyl (5-(tert-butyldimethylsilanyloxy)-4-phenylselanyl)-(E)-pent-2-enoate
• CAS No.: 1265627-80-2
• Molecular Formula: C₁₉H₃₀O₃SeSi
• Molecular Weight: 413.491
• Mol file: 1265627-80-2.mol

Synonyms:ethyl (5-(tert-butyldimethylsilanyloxy)-4-phenylselanyl)-(E)-pent-2-enoate

Chemical Property of ethyl (5-(tert-butyldimethylsilanyloxy)-4-phenylselanyl)-(E)-pent-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of ethyl (5-(tert-butyldimethylsilanyloxy)-4-phenylselanyl)-(E)-pent-2-enoate

There total 1 articles about ethyl (5-(tert-butyldimethylsilanyloxy)-4-phenylselanyl)-(E)-pent-2-enoate 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: 54.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + N-phenylselanylphthalimide (71098-88-9) + 3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → ethyl (5-(tert-butyldimethylsilanyloxy)-4-phenylselanyl)-(E)-pent-2-enoate (1265627-80-2)

Guidance literature:

N-phenylselanylphthalimide; 3-(tert-butyldimethylsilanyloxy)propionaldehyde; With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; 4-nitro-benzoic acid; In toluene; at 0 ℃; for 16h; Inert atmosphere;

diethoxyphosphoryl-acetic acid ethyl ester; With n-butyllithium; In hexane; dichloromethane; at -70 - 0 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol1030926

Reference yield: 97.0%

ethyl (5-(tert-butyldimethylsilanyloxy)-4-phenylselanyl)-(E)-pent-2-enoate (1265627-80-2) → C13H16O3Se (1265628-03-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 55 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol1030926

Reference yield: 57.0%

O-benzyl carbamate (621-84-1) + ethyl (5-(tert-butyldimethylsilanyloxy)-4-phenylselanyl)-(E)-pent-2-enoate (1265627-80-2) → ethyl 2-benzyloxycarbonylamino-5-hydroxy-(E)-pent-3-enoate (1265627-94-8)

Guidance literature:

O-benzyl carbamate; ethyl (5-(tert-butyldimethylsilanyloxy)-4-phenylselanyl)-(E)-pent-2-enoate; With toluene-4-sulfonic acid; trimethyl orthoformate; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

With N-chloro-succinimide; N-ethyl-N,N-diisopropylamine; In methanol; for 0.0833333h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ol1030926

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

N-phenylselanylphthalimide

3-(tert-butyldimethylsilanyloxy)propionaldehyde

Downstream raw materials:

C₁₃H₁₆O₃Se

ethyl 2-benzyloxycarbonylamino-5-hydroxy-(E)-pent-3-enoate