(3R,4S)-4-[(R)-2-carboxymethyl-1-hydroxy-2-propenyl]-3-phenoxy-1-(2-propenyl)-2-azetidinone

Base Information

Chemical Name:(3R,4S)-4-[(R)-2-carboxymethyl-1-hydroxy-2-propenyl]-3-phenoxy-1-(2-propenyl)-2-azetidinone
CAS No.:331258-68-5
Molecular Formula:C₁₇H₁₉NO₅
Molecular Weight:317.342
Hs Code.:

Synonyms:(3R,4S)-4-[(R)-2-carboxymethyl-1-hydroxy-2-propenyl]-3-phenoxy-1-(2-propenyl)-2-azetidinone

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Chemical Property of (3R,4S)-4-[(R)-2-carboxymethyl-1-hydroxy-2-propenyl]-3-phenoxy-1-(2-propenyl)-2-azetidinone

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Technology Process of (3R,4S)-4-[(R)-2-carboxymethyl-1-hydroxy-2-propenyl]-3-phenoxy-1-(2-propenyl)-2-azetidinone

There total 5 articles about (3R,4S)-4-[(R)-2-carboxymethyl-1-hydroxy-2-propenyl]-3-phenoxy-1-(2-propenyl)-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: 58.0%

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: 201748-24-5
(+)-(3R,4S)-4-formyl-3-phenoxy-1-(2-propenyl)-2-azetidinone

: 331258-68-5
(3R,4S)-4-[(R)-2-carboxymethyl-1-hydroxy-2-propenyl]-3-phenoxy-1-(2-propenyl)-2-azetidinone

Guidance literature:: With 1,4-diaza-bicyclo[2.2.2]octane; In acetonitrile; at -20 ℃; for 120h;
DOI:10.1021/jo005715z

Reference yield:

: 701-99-5
Phenoxyacetyl chloride

: 331258-68-5
(3R,4S)-4-[(R)-2-carboxymethyl-1-hydroxy-2-propenyl]-3-phenoxy-1-(2-propenyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine / CH₂Cl₂ / 16 h / 20 °C

2: p-TsOH*H₂O / tetrahydrofuran / 2 h / Heating

3: sodium periodate; sodium hydrogen carbonate / CH₂Cl₂ / 2 h / 20 °C

4: 58 percent / DABCO / acetonitrile / 120 h / -20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; sodium periodate; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Staudinger reaction / 4: Baylis-Hillman reaction;
DOI:10.1021/jo005715z

Reference yield:

: 214477-58-4
(3R,4S)-4-[(1S)-1,2-dihydroxyethyl]-3-phenoxy-1-allylazetidin-2-one

: 331258-68-5
(3R,4S)-4-[(R)-2-carboxymethyl-1-hydroxy-2-propenyl]-3-phenoxy-1-(2-propenyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 2 steps

1: sodium periodate; sodium hydrogen carbonate / CH₂Cl₂ / 2 h / 20 °C

2: 58 percent / DABCO / acetonitrile / 120 h / -20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; sodium periodate; sodium hydrogencarbonate; In dichloromethane; acetonitrile; 2: Baylis-Hillman reaction;
DOI:10.1021/jo005715z