6-(Methyoxymethylene)penicillanic acid

Base Information

• Chemical Name: 6-(Methyoxymethylene)penicillanic acid
• CAS No.: 93040-42-7
• Molecular Formula: C₁₀H₁₃NO₄S
• Molecular Weight: 243.284
• Mol file: 93040-42-7.mol

Synonyms:6-(methyoxymethylene)penicillanic acid;6-(methyoxymethylene)penicillanic acid, (2S-(2alpha,5alpha,6E))-isomer;6-(methyoxymethylene)penicillanic acid, ammonium salt, (2s-(2alpha,5alpha,6E))-isomer;6-(methyoxymethylene)penicillanic acid, ammonium salt, (2S-2alpha,5alpha,6Z)-isomer;6-(methyoxymethylene)penicillanic acid, potassium salt, (2S-(2alpha,5alpha,6E))-isomer;6-(methyoxymethylene)penicillanic acid, potassium salt, (2S-(2alpha,5alpha,6Z))-isomer;6-MMPC

Chemical Property of 6-(Methyoxymethylene)penicillanic acid

Chemical Property:

• Vapor Pressure: 5.1E-11mmHg at 25°C
• Boiling Point: 491.9°Cat760mmHg
• Flash Point: 251.3°C
• PSA: 92.14000
• Density: 1.43g/cm³
• LogP: 0.60150
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 243.05652907
• Heavy Atom Count: 16
• Complexity: 390

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(=COC)C2=O)C(=O)O)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)/C(=C\OC)/C2=O)C(=O)O)C

Technology Process of 6-(Methyoxymethylene)penicillanic acid

There total 5 articles about 6-(Methyoxymethylene)penicillanic acid 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,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (51056-25-8) → 6-<(Z)-methoxymethylene>penicillanic acid (93040-42-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) DMSO, N,N'-dicyclohexylcarbodiimide, dichloroacetic acid, 2.) oxalic acid / 1.) benzene, 10 min, 2.) ether, MeOH

2: 1.) sec-butyllithium / 1.) THF, cyclohexane, -23 deg C, 15 min, 2.) -78 deg C, 3 h

3: 85 percent / Et₃N, 4-(dimethylamino)pyridine / 4 h / 25 °C

4: 93 percent / H₂ / 10percent Pd/C / ethyl acetate / 5 h / 25 °C / 2585.7 Torr

5: CsF / dimethylsulfoxide / 2 h / 80 °C

With dichloro-acetic acid; dmap; hydrogen; sec.-butyllithium; oxalic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; cesium fluoride; palladium on activated charcoal; In dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/jo00201a004

Reference yield:

6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-hydroxypenicillanic acid benzyl ester (93756-62-8) → 6-<(Z)-methoxymethylene>penicillanic acid (93040-42-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Et₃N, 4-(dimethylamino)pyridine / 4 h / 25 °C

2: 93 percent / H₂ / 10percent Pd/C / ethyl acetate / 5 h / 25 °C / 2585.7 Torr

3: CsF / dimethylsulfoxide / 2 h / 80 °C

With dmap; hydrogen; triethylamine; cesium fluoride; palladium on activated charcoal; In dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/jo00201a004

Reference yield:

6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid benzyl ester (93756-63-9) → 6-<(Z)-methoxymethylene>penicillanic acid (93040-42-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / H₂ / 10percent Pd/C / ethyl acetate / 5 h / 25 °C / 2585.7 Torr

2: CsF / dimethylsulfoxide / 2 h / 80 °C

With hydrogen; cesium fluoride; palladium on activated charcoal; In dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/jo00201a004

upstream raw materials:

6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid

(2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-hydroxypenicillanic acid benzyl ester

6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid benzyl ester

Refernces