(3S,4R)-4-(4-benzoyloxybut-2-ynyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone

Base Information

Chemical Name:(3S,4R)-4-(4-benzoyloxybut-2-ynyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone
CAS No.:362605-36-5
Molecular Formula:C₂₂H₃₁NO₄Si
Molecular Weight:401.578
Hs Code.:

Synonyms:(3S,4R)-4-(4-benzoyloxybut-2-ynyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone

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Chemical Property of (3S,4R)-4-(4-benzoyloxybut-2-ynyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone

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Technology Process of (3S,4R)-4-(4-benzoyloxybut-2-ynyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone

There total 7 articles about (3S,4R)-4-(4-benzoyloxybut-2-ynyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-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: 94.0%

: 98-88-4
benzoyl chloride

: 457068-80-3
(3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-(4-hydroxybut-2-ynyl)-2-azetidinone

: 362605-36-5
(3S,4R)-4-(4-benzoyloxybut-2-ynyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/jo030123c

Reference yield: 44.0%

: 532-32-1
sodium benzoate

: 362605-47-8
phosphoric acid 4-{(3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-oxo-4-azetidinyl}but-2-ynyl ester diethyl ester

: (5R,6S)-6-[(R)-1-tert-butyldimethylsilyloxyethyl]-3-methylidene-carbapen-1-em

: Benzoic acid (5R,6S)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methylene-7-oxo-1-aza-bicyclo[3.2.0]hept-3-yl ester

: 362605-36-5
(3S,4R)-4-(4-benzoyloxybut-2-ynyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone

Guidance literature:: With 1,1'-bis-(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; at 55 ℃; for 5h;
DOI:10.1016/S0040-4039(01)00870-X

Reference yield:

: 80433-47-2
(3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-(prop-2-enyl)-2-azetidinone

: 362605-36-5
(3S,4R)-4-(4-benzoyloxybut-2-ynyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / Et₃N; NaI / dimethylformamide / 10 h / 20 °C

2.1: O₃/O₂ / CH₂Cl₂ / -78 °C

2.2: 95 percent / PPh₃ / CH₂Cl₂ / 12 h / 20 °C

3.1: 87 percent / Et₃N; PPh₃ / CH₂Cl₂ / 1 h / 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 82 percent / tetrahydrofuran; hexane / 4 h / 0 °C

5.1: 95 percent / KF / methanol / 1 h / 0 °C

6.1: 94 percent / pyridine / CH₂Cl₂ / 4 h / 20 °C

With pyridine; potassium fluoride; n-butyllithium; oxygen; ozone; triethylamine; triphenylphosphine; sodium iodide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo030123c