Carbonic acid benzyl ester (R)-1-[(3S,4R)-2-oxo-4-((R)-2-oxo-cyclohexyl)-azetidin-3-yl]-ethyl ester

Base Information

• Chemical Name: Carbonic acid benzyl ester (R)-1-[(3S,4R)-2-oxo-4-((R)-2-oxo-cyclohexyl)-azetidin-3-yl]-ethyl ester
• CAS No.: 219603-19-7
• Molecular Formula: C₁₉H₂₃NO₅
• Molecular Weight: 345.395
• Mol file: 219603-19-7.mol

Synonyms:Carbonic acid benzyl ester (R)-1-[(3S,4R)-2-oxo-4-((R)-2-oxo-cyclohexyl)-azetidin-3-yl]-ethyl ester

Chemical Property of Carbonic acid benzyl ester (R)-1-[(3S,4R)-2-oxo-4-((R)-2-oxo-cyclohexyl)-azetidin-3-yl]-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid benzyl ester (R)-1-[(3S,4R)-2-oxo-4-((R)-2-oxo-cyclohexyl)-azetidin-3-yl]-ethyl ester

There total 13 articles about Carbonic acid benzyl ester (R)-1-[(3S,4R)-2-oxo-4-((R)-2-oxo-cyclohexyl)-azetidin-3-yl]-ethyl 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: 91.0%

Carbonic acid benzyl ester (R)-1-[(2R,3S)-2-((1R,2R)-2-hydroxy-cyclohexyl)-4-oxo-azetidin-3-yl]-ethyl ester → Carbonic acid benzyl ester (R)-1-[(3S,4R)-2-oxo-4-((R)-2-oxo-cyclohexyl)-azetidin-3-yl]-ethyl ester (219603-19-7)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(98)02055-3

Reference yield:

3,4-dihydro-spiro[benzo[e][1,3]oxazine-2,1'-cyclohexane] (14783-46-1) → Carbonic acid benzyl ester (R)-1-[(3S,4R)-2-oxo-4-((R)-2-oxo-cyclohexyl)-azetidin-3-yl]-ethyl ester (219603-19-7)

Guidance literature:

Multi-step reaction with 12 steps

1: PhNMe₂

2: 91 percent / p-AcNHC₆H₄SO₂N₃, DBU / acetonitrile

3: dirhodium(II) tetrakis / toluene / 96 h / 0 °C

4: 82 percent / LiBH₄ / tetrahydrofuran / 2 h / 0 °C

5: 57 percent / hydrogen / RhCl₃-methyltrioctylammonium chloride / 1,2-dichloro-ethane; H₂O / 38 h / 25 °C

6: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

7: 83 percent / CH₂Cl₂ / 2 h / 0 °C

8: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

9: 79 percent / K-Selectride / tetrahydrofuran / 1.5 h / 0 °C

10: 89 percent / DMAP, Et₃N / CH₂Cl₂ / 3 h

11: aq. AcOH / 6 h / 70 °C

12: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

With dmap; lithium borohydride; dirhodium(II) tetrakis(N-phthaloyl-(S)-alaninate); 4-acetamidobenzenesulfonyl azide; hydrogen; potassium tri-sec-butyl-borohydride; Dess-Martin periodane; acetic acid; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; rhodium(III) chloride; Aliquat 336; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0040-4039(98)02055-3

Reference yield:

2-Hydroxybenzylamine (932-30-9) → Carbonic acid benzyl ester (R)-1-[(3S,4R)-2-oxo-4-((R)-2-oxo-cyclohexyl)-azetidin-3-yl]-ethyl ester (219603-19-7)

Guidance literature:

Multi-step reaction with 13 steps

1: toluene / Heating

2: PhNMe₂

3: 91 percent / p-AcNHC₆H₄SO₂N₃, DBU / acetonitrile

4: dirhodium(II) tetrakis / toluene / 96 h / 0 °C

5: 82 percent / LiBH₄ / tetrahydrofuran / 2 h / 0 °C

6: 57 percent / hydrogen / RhCl₃-methyltrioctylammonium chloride / 1,2-dichloro-ethane; H₂O / 38 h / 25 °C

7: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

8: 83 percent / CH₂Cl₂ / 2 h / 0 °C

9: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

10: 79 percent / K-Selectride / tetrahydrofuran / 1.5 h / 0 °C

11: 89 percent / DMAP, Et₃N / CH₂Cl₂ / 3 h

12: aq. AcOH / 6 h / 70 °C

13: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

With dmap; lithium borohydride; dirhodium(II) tetrakis(N-phthaloyl-(S)-alaninate); 4-acetamidobenzenesulfonyl azide; hydrogen; potassium tri-sec-butyl-borohydride; Dess-Martin periodane; acetic acid; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; rhodium(III) chloride; Aliquat 336; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0040-4039(98)02055-3

upstream raw materials:

3,4-dihydro-spiro[benzo[e][1,3]oxazine-2,1'-cyclohexane]

2-Hydroxybenzylamine

C₁₇H₂₅NO₃

C₁₇H₂₁NO₄

Downstream raw materials:

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((R)-2-oxo-cyclohexyl)-azetidin-2-one