(3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

Base Information

Chemical Name:(3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone
CAS No.:277757-95-6
Molecular Formula:C₁₇H₂₁NO₄
Molecular Weight:303.358
Hs Code.:

Synonyms:(3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

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Chemical Property of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

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Technology Process of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

There total 6 articles about (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-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: 71.0%

: 221909-59-7
(+)-(3R,4R)-4-formyl-3-allyloxy-1-(p-methoxyphenyl)-2-azetidinone

: 762-72-1
allyl-trimethyl-silane

: 277757-95-6
(3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

: (3R,4S)-4-[(S)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -78 ℃; for 0.75h;
DOI:10.1021/jo991641j

Reference yield:

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

: 277757-95-6
(3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: 70 percent / sodium hydroxide; tetrabutyl ammonium iodide / CH₂Cl₂; H₂O / 20 h / 20 °C

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

5: sodium hydrogen carbonate; sodium periodate / CH₂Cl₂; H₂O / 2 h

6: 71 percent / SnCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

With sodium hydroxide; sodium periodate; sodium methylate; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1: Staudinger reaction / 2: Deacetylation / 3: Alkylation / 4: Hydrolysis / 5: oxidative cleavage / 6: Addition;
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

: 277757-95-6
(3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / sodium hydroxide; tetrabutyl ammonium iodide / CH₂Cl₂; H₂O / 20 h / 20 °C

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

3: sodium hydrogen carbonate; sodium periodate / CH₂Cl₂; H₂O / 2 h

4: 71 percent / SnCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

With sodium hydroxide; sodium periodate; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; 1: Alkylation / 2: Hydrolysis / 3: oxidative cleavage / 4: Addition;
DOI:10.1021/jo991641j