allyl (4R,5S,6S)-3-benzylthio-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Base Information

Chemical Name:allyl (4R,5S,6S)-3-benzylthio-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
CAS No.:144837-72-9
Molecular Formula:C₂₆H₃₇NO₄SSi
Molecular Weight:487.736
Hs Code.:

Synonyms:allyl (4R,5S,6S)-3-benzylthio-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Chemical Property of allyl (4R,5S,6S)-3-benzylthio-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Technology Process of allyl (4R,5S,6S)-3-benzylthio-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

There total 9 articles about allyl (4R,5S,6S)-3-benzylthio-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 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: 72.0%

: 163166-93-6
(3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-benzylthiocarbonylethyl]-2-azetidinone

: 144837-72-9
allyl (4R,5S,6S)-3-benzylthio-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: With tributyl-amine; titanium tetrachloride; In dichloromethane; at -45 - -40 ℃; for 1h;
DOI:10.1002/adsc.200303065

Reference yield:

: 153976-18-2
(3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-carboxyethyl]-2-azetidinone

: 144837-72-9
allyl (4R,5S,6S)-3-benzylthio-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / benzene / 0.5 h / 20 - 25 °C

1.2: 66 percent / benzene / 12 h

2.1: 72 percent / Bu₃N / TiCl₄ / CH₂Cl₂ / 1 h / -45 - -40 °C

With dmap; tributyl-amine; dicyclohexyl-carbodiimide; titanium tetrachloride; In dichloromethane; benzene; 2.1: Ti-Dieckmann condensation;
DOI:10.1002/adsc.200303065

Reference yield:

: 100-53-8
phenylmethanethiol

: 144837-72-9
allyl (4R,5S,6S)-3-benzylthio-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / benzene / 0.5 h / 20 - 25 °C

1.2: 66 percent / benzene / 12 h

2.1: 72 percent / Bu₃N / TiCl₄ / CH₂Cl₂ / 1 h / -45 - -40 °C

With dmap; tributyl-amine; dicyclohexyl-carbodiimide; titanium tetrachloride; In dichloromethane; benzene; 2.1: Ti-Dieckmann condensation;
DOI:10.1002/adsc.200303065