(+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone

Base Information

Chemical Name:(+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone
CAS No.:277757-85-4
Molecular Formula:C₁₆H₁₉NO₇
Molecular Weight:337.329
Hs Code.:

Synonyms:(+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone

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Chemical Property of (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone

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Technology Process of (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone

There total 4 articles about (+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone 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: 100.0%

: 277757-28-5
(+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone

: 277757-85-4
(+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone

Guidance literature:: With toluene-4-sulfonic acid; In tetrahydrofuran; water; for 2h; Heating;
DOI:10.1021/jo991641j

Reference yield:

: 103239-04-9
N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine

: 277757-85-4
(+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

2: 95 percent / sodium methoxide / methanol / 0.33 h / 20 °C

3: 72 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: 100 percent / p-TsOH*H₂O / tetrahydrofuran; H₂O / 2 h / Heating

With sodium methylate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1: Staudinger reaction / 2: Deacetylation / 3: Addition / 4: Hydrolysis;
DOI:10.1021/jo991641j

Reference yield:

: 115828-87-0
(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

: 277757-85-4
(+)-(3R,4S)-3-(2-carboxymethyl-1-ethenyloxy)-4-[(S)-1,2-dihydroxyethylen]-1-(p-methoxyphenyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 100 percent / p-TsOH*H₂O / tetrahydrofuran; H₂O / 2 h / Heating

With toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; 1: Addition / 2: Hydrolysis;
DOI:10.1021/jo991641j