allyl (6S,7S)-8-oxo-3-<2-(phenylseleno)ethyl>-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Base Information

• Chemical Name: allyl (6S,7S)-8-oxo-3-<2-(phenylseleno)ethyl>-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
• CAS No.: 113599-77-2
• Molecular Formula: C₃₇H₃₄N₂O₄Se
• Molecular Weight: 649.648
• Mol file: 113599-77-2.mol

Synonyms:allyl (6S,7S)-8-oxo-3-<2-(phenylseleno)ethyl>-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Chemical Property of allyl (6S,7S)-8-oxo-3-<2-(phenylseleno)ethyl>-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl (6S,7S)-8-oxo-3-<2-(phenylseleno)ethyl>-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

There total 8 articles about allyl (6S,7S)-8-oxo-3-<2-(phenylseleno)ethyl>-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate 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: 73.0%

allyl 2-<(3S,4S)-4-(hydroxymethyl)-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-5-(phenylseleno)pentanoate (113599-70-5) → allyl (6S,7S)-8-oxo-3-<2-(phenylseleno)ethyl>-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-77-2)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 0.25h;

DOI:10.1021/jm00401a020

Reference yield:

allyl bromoacetate (40630-84-0) → allyl (6S,7S)-8-oxo-3-<2-(phenylseleno)ethyl>-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-77-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 59 percent / tetrabutylammonium bromide, KOH / tetrahydrofuran / 20 h

2: 48 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / -78 °C

3: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

4: 73 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 0.25 h

With potassium hydroxide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jm00401a020

Reference yield:

3-(phenylselanyl)propanoic acid (16599-78-3) → allyl (6S,7S)-8-oxo-3-<2-(phenylseleno)ethyl>-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-77-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / oxalyl chloride / 4 h

2: 48 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / -78 °C

3: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

4: 73 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 0.25 h

With oxalyl dichloride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jm00401a020

upstream raw materials:

allyl 2-<(3S,4S)-4-(hydroxymethyl)-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-5-(phenylseleno)pentanoate

allyl bromoacetate

3-(phenylselanyl)propanoic acid

trityl chloride

Downstream raw materials:

allyl (6S,7S)-7-amino-3-<2-(phenylseleno)ethyl>-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate p-toluenesulfonic acid salt