(1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester
• CAS No.: 129416-16-6
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.507

Synonyms:

Chemical Property of (1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

There total 23 articles about (1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester 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:

2-amino-1-(3-methoxyphenyl)ethanol (27382-18-9) → (1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester (129416-16-6,129446-81-7)

Guidance literature:

Multi-step reaction with 21 steps

1: 93 percent / pyridine / CH₂Cl₂ / 0 °C

2: 90 percent / KH / tetrahydrofuran

3: 4 N NaOH / ethanol / Heating

4: DMAP, iPr₂NEt / CH₂Cl₂

5: 96 percent / NEt₃ / CH₂Cl₂ / 0 °C

6: tetrahydrofuran / 60 °C

7: 1 N HCl / tetrahydrofuran

8: 91 percent / sodium cyanoborohydride / ethanol; tetrahydrofuran; acetic acid / -20 deg C to room temperature

9: 88 percent / iPrNEt₂ / CH₂Cl₂

10: RedAl / tetrahydrofuran / -78 to -50 deg C

11: PPTS

12: Bu₄NF / tetrahydrofuran

13: Swern oxidation

14: KH / tetrahydrofuran; triethylamine / 0 °C

15: 48 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / 0 deg C to room temperature

16: 81 percent / RhCl(PPh₃)3 / toluene / Heating

17: 1.) O₃, 2.) Me₂S / MeOH

18: NaHCO₃

19: 84 percent / NaBH₄ / methanol

20: SOCl₂, pyridine

21: DBU / toluene / Heating

With pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; dimethylsulfide; N,N-diethyl-N-isopropylamine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; triethylamine; toluene;

DOI:10.1016/0040-4039(90)80083-X

Reference yield:

2-Allylamino-1-(3-methoxy-phenyl)-ethanol → (1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester (129416-16-6,129446-81-7)

Guidance literature:

Multi-step reaction with 18 steps

1: DMAP, iPr₂NEt / CH₂Cl₂

2: 96 percent / NEt₃ / CH₂Cl₂ / 0 °C

3: tetrahydrofuran / 60 °C

4: 1 N HCl / tetrahydrofuran

5: 91 percent / sodium cyanoborohydride / ethanol; tetrahydrofuran; acetic acid / -20 deg C to room temperature

6: 88 percent / iPrNEt₂ / CH₂Cl₂

7: RedAl / tetrahydrofuran / -78 to -50 deg C

8: PPTS

9: Bu₄NF / tetrahydrofuran

10: Swern oxidation

11: KH / tetrahydrofuran; triethylamine / 0 °C

12: 48 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / 0 deg C to room temperature

13: 81 percent / RhCl(PPh₃)3 / toluene / Heating

14: 1.) O₃, 2.) Me₂S / MeOH

15: NaHCO₃

16: 84 percent / NaBH₄ / methanol

17: SOCl₂, pyridine

18: DBU / toluene / Heating

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; thionyl chloride; dimethylsulfide; N,N-diethyl-N-isopropylamine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; triethylamine; toluene;

DOI:10.1016/0040-4039(90)80083-X

Reference yield:

5-(3-Methoxy-phenyl)-oxazolidin-2-one (129416-01-9) → (1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester (129416-16-6,129446-81-7)

Guidance literature:

Multi-step reaction with 20 steps

1: 90 percent / KH / tetrahydrofuran

2: 4 N NaOH / ethanol / Heating

3: DMAP, iPr₂NEt / CH₂Cl₂

4: 96 percent / NEt₃ / CH₂Cl₂ / 0 °C

5: tetrahydrofuran / 60 °C

6: 1 N HCl / tetrahydrofuran

7: 91 percent / sodium cyanoborohydride / ethanol; tetrahydrofuran; acetic acid / -20 deg C to room temperature

8: 88 percent / iPrNEt₂ / CH₂Cl₂

9: RedAl / tetrahydrofuran / -78 to -50 deg C

10: PPTS

11: Bu₄NF / tetrahydrofuran

12: Swern oxidation

13: KH / tetrahydrofuran; triethylamine / 0 °C

14: 48 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / 0 deg C to room temperature

15: 81 percent / RhCl(PPh₃)3 / toluene / Heating

16: 1.) O₃, 2.) Me₂S / MeOH

17: NaHCO₃

18: 84 percent / NaBH₄ / methanol

19: SOCl₂, pyridine

20: DBU / toluene / Heating

With pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; dimethylsulfide; N,N-diethyl-N-isopropylamine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; triethylamine; toluene;

DOI:10.1016/0040-4039(90)80083-X

upstream raw materials:

2-amino-1-(3-methoxyphenyl)ethanol

5-(3-Methoxy-phenyl)-oxazolidin-2-one

(tert-Butyl-dimethyl-silanyloxy)-(3-methoxy-phenyl)-acetonitrile

3-Allyl-5-(3-methoxy-phenyl)-oxazolidin-2-one

Downstream raw materials:

(1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one

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