allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Base Information

Chemical Name:allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
CAS No.:113599-91-0
Molecular Formula:C₂₅H₂₇N₃O₈
Molecular Weight:497.505
Hs Code.:

Synonyms:allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

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Chemical Property of allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

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Technology Process of allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

There total 9 articles about allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-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:

: 40630-84-0
allyl bromoacetate

: 113599-91-0
allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

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

2: 76 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C

3: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran

4: 91 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran

5: 1.) p-toluenesulfonic acid monohydrate, 2.) sodium bicarbonate, pH 8 / 1.) acetone, 19 h, 2.) EtOAc, H₂O

6: EEDQ / ethyl acetate / 3 h / Ambient temperature

7: 1.) m-CPBA, 2.) pyridine, dihydropyran / 1.) CHCl₃, 1,1,1-trichloroethane, -15 deg C, 0.5 h, 2.) reflux, 1.5 h

With pyridine; 3,4-dihydro-2H-pyran; potassium hydroxide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate;
DOI:10.1021/jm00401a020

Reference yield:

: 22818-40-2
D-4-hydroxyphenylglycine

: 113599-91-0
allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 50 percent / 1N NaOH / diethyl ether; H₂O; dioxane / 1 h / ice bath

2: EEDQ / ethyl acetate / 3 h / Ambient temperature

3: 1.) m-CPBA, 2.) pyridine, dihydropyran / 1.) CHCl₃, 1,1,1-trichloroethane, -15 deg C, 0.5 h, 2.) reflux, 1.5 h

With pyridine; 3,4-dihydro-2H-pyran; sodium hydroxide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; diethyl ether; water; ethyl acetate;
DOI:10.1021/jm00401a020

Reference yield:

: 84792-41-6
(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine

: 113599-91-0
allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: EEDQ / ethyl acetate / 3 h / Ambient temperature

2: 1.) m-CPBA, 2.) pyridine, dihydropyran / 1.) CHCl₃, 1,1,1-trichloroethane, -15 deg C, 0.5 h, 2.) reflux, 1.5 h

With pyridine; 3,4-dihydro-2H-pyran; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 3-chloro-benzenecarboperoxoic acid; In ethyl acetate;
DOI:10.1021/jm00401a020