(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

Base Information

Chemical Name:(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
CAS No.:113599-92-1
Molecular Formula:C₂₃H₂₄IN₃O₈
Molecular Weight:597.363
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 9 articles about (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 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

: 113599-92-1
(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

Guidance literature:: Multi-step reaction with 7 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

7: NaI / acetone / 2 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; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate; acetone;
DOI:10.1021/jm00401a020

Reference yield:

: 113599-84-1
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

: 113599-92-1
(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

Guidance literature:: With sodium iodide; In acetone; for 2h; Ambient temperature;
DOI:10.1021/jm00401a020

Reference yield:

: 22818-40-2
D-4-hydroxyphenylglycine

: 113599-92-1
(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

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: NaI / acetone / 2 h / Ambient temperature

With sodium hydroxide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium iodide; In 1,4-dioxane; diethyl ether; water; ethyl acetate; acetone;
DOI:10.1021/jm00401a020