(5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-7-oxo-3-(pyridin-4-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-7-oxo-3-(pyridin-4-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 112545-79-6
• Molecular Formula: C₂₂H₁₉N₃O₈S
• Molecular Weight: 485.474
• Mol file: 112545-79-6.mol

Synonyms:

Chemical Property of (5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-7-oxo-3-(pyridin-4-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-7-oxo-3-(pyridin-4-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 11 articles about (5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-7-oxo-3-(pyridin-4-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-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:

(2S,3R)-Oxirane-2,3-dicarboxylic acid monomethyl ester (63544-00-3,66647-19-6,96096-72-9,110115-15-6,110115-16-7,112574-71-7,119240-65-2,150134-07-9,150134-08-0) → (5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-7-oxo-3-(pyridin-4-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (112545-79-6,114376-71-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / DCC / tetrahydrofuran / 0.5 h / Ambient temperature

2: 58 percent / Bu₄NF, sieves 4 Angstroem / tetrahydrofuran / 1.2 h / 0 °C

3: 82 percent / TFA / CH₂Cl₂ / 3 h / Ambient temperature

4: 47 percent / Pb(OAc)4 / dimethylformamide / 0.12 h / 60 °C

5: 86 percent / DMAP / dimethylformamide / 22 h / Ambient temperature

6: 78 percent / ceric (IV) ammonium nitrate / acetonitrile; H₂O / 0 °C

7: 64 percent / NEt₃, trimethylsilyltrifluormethanesulphonate / 0 deg C to room temp.

8: 89 percent / BF₃*Et₂O / acetonitrile / 1 h / 0 °C

9: 57 percent / Rh₂(OAc)4 / CH₂Cl₂ / Heating

10: 1) i-Pr₂NEt, (PhO)2POCl, / 1) CH₃CN, 0 deg C, 15 min, 2) -40 to 0 deg C

With lead(IV) acetate; dmap; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; chlorophosphoric acid diphenyl ester; trifluoroacetic acid; dirhodium tetraacetate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(01)80988-6

Reference yield:

(R)-((2S,3S)-2-Acetoxy-4-oxo-azetidin-3-yl)-(tert-butyl-dimethyl-silanyloxy)-acetic acid methyl ester (112545-75-2,114376-67-9) → (5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-7-oxo-3-(pyridin-4-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (112545-79-6,114376-71-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / NEt₃, trimethylsilyltrifluormethanesulphonate / 0 deg C to room temp.

2: 89 percent / BF₃*Et₂O / acetonitrile / 1 h / 0 °C

3: 57 percent / Rh₂(OAc)4 / CH₂Cl₂ / Heating

4: 1) i-Pr₂NEt, (PhO)2POCl, / 1) CH₃CN, 0 deg C, 15 min, 2) -40 to 0 deg C

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; triethylamine; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; dirhodium tetraacetate; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(01)80988-6

Reference yield:

(2S,3S)-3-((S)-Hydroxy-methoxycarbonyl-methyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid (112545-72-9,114376-64-6) → (5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-7-oxo-3-(pyridin-4-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (112545-79-6,114376-71-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 47 percent / Pb(OAc)4 / dimethylformamide / 0.12 h / 60 °C

2: 86 percent / DMAP / dimethylformamide / 22 h / Ambient temperature

3: 78 percent / ceric (IV) ammonium nitrate / acetonitrile; H₂O / 0 °C

4: 64 percent / NEt₃, trimethylsilyltrifluormethanesulphonate / 0 deg C to room temp.

5: 89 percent / BF₃*Et₂O / acetonitrile / 1 h / 0 °C

6: 57 percent / Rh₂(OAc)4 / CH₂Cl₂ / Heating

7: 1) i-Pr₂NEt, (PhO)2POCl, / 1) CH₃CN, 0 deg C, 15 min, 2) -40 to 0 deg C

With lead(IV) acetate; dmap; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; triethylamine; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; dirhodium tetraacetate; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(01)80988-6

upstream raw materials:

pyridine-4-thiol

(2R,5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

(2S,3R)-Oxirane-2,3-dicarboxylic acid monomethyl ester

(R)-((2S,3S)-2-Acetoxy-4-oxo-azetidin-3-yl)-(tert-butyl-dimethyl-silanyloxy)-acetic acid methyl ester