(3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone

Base Information

Chemical Name:(3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone
CAS No.:251480-07-6
Molecular Formula:C₁₉H₂₁NO₄
Molecular Weight:327.38
Hs Code.:

Synonyms:(3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone

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Chemical Property of (3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone

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Technology Process of (3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone

There total 5 articles about (3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-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: 60.0%

: 78-94-4,25038-87-3
methyl vinyl ketone

: 251480-04-3
(+)-(2R,3R)-1-(4-pentynyl)-3-phenoxy-4-oxoazetidine-2-carbaldehyde

: 251480-07-6
(3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone

Guidance literature:: With 1,4-diaza-bicyclo[2.2.2]octane; In acetonitrile; at -20 ℃;
DOI:10.1039/a905017e

Reference yield:

: 701-99-5
Phenoxyacetyl chloride

: 251480-07-6
(3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 68 percent / triethylamine / CH₂Cl₂ / 16 h / 20 °C

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

3: 806 mg / sodium periodate; sodium hydrogen carbonate / CH₂Cl₂ / 2 h / 20 °C

4: 60 percent / DABCO / acetonitrile / 48 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:

: N-(4-pentynyl)-2,3-O-(isopropylidene)-D-glyceraldehyde imine

: 251480-07-6
(3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-1-(4-pentynyl)-3-phenoxy-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 68 percent / triethylamine / CH₂Cl₂ / 16 h / 20 °C

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

3: 806 mg / sodium periodate; sodium hydrogen carbonate / CH₂Cl₂ / 2 h / 20 °C

4: 60 percent / DABCO / acetonitrile / 48 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