<3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone

Base Information

• Chemical Name: <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone
• CAS No.: 101977-77-9
• Molecular Formula: C₂₀H₂₁NO₃
• Molecular Weight: 323.392
• Mol file: 101977-77-9.mol

Synonyms:<3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone

Chemical Property of <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone

There total 11 articles about <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-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: 77.0%

ethyl 3-hydroxybutyrate (5405-41-4) + (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline (88315-63-3) → 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one (100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6)

Guidance literature:

With lithium cyclohexylisopropylamide; In tetrahydrofuran; the reaction mixture was quenched at 10 deg C;

DOI:10.1016/S0040-4039(00)98683-0

Reference yield: 67.0%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + N-cinnamylidene-p-anisidine (80542-40-1) → 3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one (100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)96544-4

Reference yield: 25.0%

N-(4-Methoxyphenyl)-3-phenylpropenaldimine (15286-52-9,22835-33-2,80542-40-1,88315-63-3,101535-86-8,123525-44-0) + ethyl (S)-3-hydroxybutyrate (56816-01-4) → (3S,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one (100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6) + <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone (101977-77-9)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 22h; Yields of byproduct given;

DOI:10.1016/0040-4020(89)80126-7

upstream raw materials:

ethyl 3-hydroxybutyrate

(E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

N-(4-Methoxyphenyl)-3-phenylpropenaldimine

ethyl (S)-3-hydroxybutyrate

Downstream raw materials:

(2S,3S)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carbaldehyde

(1S,2S,4R,5R)-4-hydroxy-6-(4-methoxyphenyl)-2-methyl-3-oxa-6-azabicyclo(3.2.0)heptan-7-one

(3R,4S(E))-3-(1(S)-(((1,1-dimethylethyl)dimethylsilyl)oxy)ethyl)-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone

(1'S,3S,4R)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone