(+)-(5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-1-methoxy-5,6-dihydropyridin-2(1H)-one

Base Information

Chemical Name:(+)-(5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-1-methoxy-5,6-dihydropyridin-2(1H)-one
CAS No.:1304540-38-2
Molecular Formula:C₁₄H₁₇NO₄
Molecular Weight:263.293
Hs Code.:

Synonyms:(+)-(5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-1-methoxy-5,6-dihydropyridin-2(1H)-one

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Chemical Property of (+)-(5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-1-methoxy-5,6-dihydropyridin-2(1H)-one

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Technology Process of (+)-(5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-1-methoxy-5,6-dihydropyridin-2(1H)-one

There total 6 articles about (+)-(5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-1-methoxy-5,6-dihydropyridin-2(1H)-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: 62.0%

: 1304540-36-0
C₁₄H₁₇NO₄

: 1304540-38-2
(+)-(5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-1-methoxy-5,6-dihydropyridin-2(1H)-one

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 16h; Inert atmosphere;
DOI:10.1021/ol200688d

Reference yield:

: (2E)-4-[(phenylmethyl)oxy]-2-buten-1-yl methyl carbonate

: 1304540-38-2
(+)-(5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-1-methoxy-5,6-dihydropyridin-2(1H)-one

Guidance literature:: Multi-step reaction with 6 steps

1: [O,O’-((S)-1,1′-dinaphthyl-2,2′-diyl)-N,N′-di-(S,S)-1-(2-methoxyphenyl)ethylphosphoramidite]; dichlorobis(η4-dibenzo[a,e]cyclooctatetraene)diiridium(I); 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 h / 50 °C / Inert atmosphere

2: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere

3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2.5 h / Inert atmosphere; Reflux

5: potassium peroxomonosulfate; sodium hydrogencarbonate / water; acetone / 6 h / 0 °C / Inert atmosphere

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; dichlorobis(η4-dibenzo[a,e]cyclooctatetraene)diiridium(I); potassium peroxomonosulfate; [O,O’-((S)-1,1′-dinaphthyl-2,2′-diyl)-N,N′-di-(S,S)-1-(2-methoxyphenyl)ethylphosphoramidite]; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene;
DOI:10.1021/ol200688d

Reference yield:

: 1304540-34-8
(-)-(6S)-6-[(benzyloxy)methyl]-1-methoxy-3,6-dihydropyridin-2(1H)-one

: 1304540-38-2
(+)-(5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-1-methoxy-5,6-dihydropyridin-2(1H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: potassium peroxomonosulfate; sodium hydrogencarbonate / water; acetone / 6 h / 0 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / Inert atmosphere

With potassium peroxomonosulfate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; acetone; toluene;
DOI:10.1021/ol200688d