allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-(chloromethyl)-8-oxo-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>-3-(chloromethyl)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
• CAS No.: 113599-84-1
• Molecular Formula: C₂₃H₂₄ClN₃O₈
• Molecular Weight: 505.912

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

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

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

allyl bromoacetate (40630-84-0) → allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-(chloromethyl)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-84-1)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 95 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / -78 °C

3: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

4: 82 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 0.25 h

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

With potassium hydroxide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jm00401a020

Reference yield:

D-4-hydroxyphenylglycine (22818-40-2) → allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-(chloromethyl)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-84-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium hydroxide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In 1,4-dioxane; diethyl ether; water; ethyl acetate;

DOI:10.1021/jm00401a020

Reference yield:

allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-78-3) → allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-(chloromethyl)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-84-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In ethyl acetate;

DOI:10.1021/jm00401a020

upstream raw materials:

(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine

(6S,7S)-7-Amino-3-chloromethyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

allyl bromoacetate

D-4-hydroxyphenylglycine

Downstream raw materials:

(6S,7S)-7-[(R)-2-Allyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-3-iodomethyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

{(6S,7S)-2-Allyloxycarbonyl-7-[(R)-2-allyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl}-triphenyl-phosphonium; iodide

(6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(cis-1-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid

(6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(trans-1-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid

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