(5S,6S)-5-acetoxy-6-benzyl-5,6-dihydro-1-[(2,4-dimethoxy)benzyl]pyridin-2-one

Base Information

Chemical Name:(5S,6S)-5-acetoxy-6-benzyl-5,6-dihydro-1-[(2,4-dimethoxy)benzyl]pyridin-2-one
CAS No.:879220-58-3
Molecular Formula:C₂₃H₂₅NO₅
Molecular Weight:395.455
Hs Code.:

Synonyms:(5S,6S)-5-acetoxy-6-benzyl-5,6-dihydro-1-[(2,4-dimethoxy)benzyl]pyridin-2-one

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Chemical Property of (5S,6S)-5-acetoxy-6-benzyl-5,6-dihydro-1-[(2,4-dimethoxy)benzyl]pyridin-2-one

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Technology Process of (5S,6S)-5-acetoxy-6-benzyl-5,6-dihydro-1-[(2,4-dimethoxy)benzyl]pyridin-2-one

There total 10 articles about (5S,6S)-5-acetoxy-6-benzyl-5,6-dihydro-1-[(2,4-dimethoxy)benzyl]pyridin-2-one 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: 95.5%

: 879220-57-2
(5S,6S)-6-benzyl-5,6-dihydro-1-[(2,4-dimethoxy)benzyl]-5-hydroxypyridin-2-one

: 108-24-7
acetic anhydride

: 879220-58-3
(5S,6S)-5-acetoxy-6-benzyl-5,6-dihydro-1-[(2,4-dimethoxy)benzyl]pyridin-2-one

Guidance literature:: With pyridine; dmap; In chloroform; at 0 ℃; for 1.5h;
DOI:10.1021/ol052781k

Reference yield:

: N-((1S,2S)-1-Benzyl-2-hydroxy-but-3-enyl)-2-nitro-benzenesulfonamide

: 879220-58-3
(5S,6S)-5-acetoxy-6-benzyl-5,6-dihydro-1-[(2,4-dimethoxy)benzyl]pyridin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 9.24 g / 2,6-lutidine / CH₂Cl₂ / 20 °C

2.1: 90.6 percent / PPh₃; DEAD / tetrahydrofuran; toluene / 20 °C

3.1: LiOH*H₂O; HSCH₂CO₂H / dimethylformamide

3.2: 60.7 percent / Et₃N / CH₂Cl₂ / cooling

4.1: 88.6 percent / TBAF / CH₂Cl₂; tetrahydrofuran

5.1: 73.6 percent / Grubbs' second-generation catalyst / CH₂Cl₂

6.1: 95.5 percent / DMAP; pyridine / CHCl₃ / cooling

With pyridine; 2,6-dimethylpyridine; dmap; lithium hydroxide; tetrabutyl ammonium fluoride; mercaptoacetic acid; triphenylphosphine; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 2.1: Mitsunobu reaction;
DOI:10.1021/jo060202z

Reference yield:

: 878440-96-1
(3S,4S)-3-[(tert-butyl)dimethylsilyloxy]-4-[N-(2-nitrobenzenesulfonyl)amino]-5-phenylpent-1-ene

: 879220-58-3
(5S,6S)-5-acetoxy-6-benzyl-5,6-dihydro-1-[(2,4-dimethoxy)benzyl]pyridin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90.6 percent / PPh₃; DEAD / tetrahydrofuran; toluene / 20 °C

2.1: LiOH*H₂O; HSCH₂CO₂H / dimethylformamide

2.2: 60.7 percent / Et₃N / CH₂Cl₂ / cooling

3.1: 88.6 percent / TBAF / CH₂Cl₂; tetrahydrofuran

4.1: 73.6 percent / Grubbs' second-generation catalyst / CH₂Cl₂

5.1: 95.5 percent / DMAP; pyridine / CHCl₃ / cooling

With pyridine; dmap; lithium hydroxide; tetrabutyl ammonium fluoride; mercaptoacetic acid; triphenylphosphine; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 1.1: Mitsunobu reaction;
DOI:10.1021/jo060202z