methyl (2S,5R,6S)-3,3-dimethyl-7-oxo-6-[(1R)-1-(2,2,2-trichloroethoxycarbonyloxy)ethyl]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Base Information

• Chemical Name: methyl (2S,5R,6S)-3,3-dimethyl-7-oxo-6-[(1R)-1-(2,2,2-trichloroethoxycarbonyloxy)ethyl]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS No.: 76431-34-0
• Molecular Formula: C14H18 Cl3 N O6 S
• Molecular Weight: 434.725
• Nikkaji Number: J319.326H
• Mol file: 76431-34-0.mol

Synonyms:

Chemical Property of methyl (2S,5R,6S)-3,3-dimethyl-7-oxo-6-[(1R)-1-(2,2,2-trichloroethoxycarbonyloxy)ethyl]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property:

• PSA: 107.44000
• LogP: 2.68770
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 432.992042
• Heavy Atom Count: 25
• Complexity: 581

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C2N(C1=O)C(C(S2)(C)C)C(=O)OC)OC(=O)OCC(Cl)(Cl)Cl
• Isomeric SMILES: C[C@H]([C@@H]1[C@@H]2N(C1=O)[C@H](C(S2)(C)C)C(=O)OC)OC(=O)OCC(Cl)(Cl)Cl

Technology Process of methyl (2S,5R,6S)-3,3-dimethyl-7-oxo-6-[(1R)-1-(2,2,2-trichloroethoxycarbonyloxy)ethyl]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

There total 4 articles about methyl (2S,5R,6S)-3,3-dimethyl-7-oxo-6-[(1R)-1-(2,2,2-trichloroethoxycarbonyloxy)ethyl]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 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:

methyl 6-α-bromo-6-β-<(1R)-hydroxyethyl>penicillanate (80629-46-5) → (2S,5R,6S)-3,3-Dimethyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester (76431-34-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / hydrogen / 10percent Pd/CaCO₃

2: pyridine / CH₂Cl₂

With pyridine; hydrogen; Lindlar's catalyst; In dichloromethane;

DOI:10.1016/S0040-4039(01)81938-9

Reference yield:

6,6-dibromopenicillanic acid (24158-88-1) → (2S,5R,6S)-3,3-Dimethyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester (76431-34-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / K₂CO₃ / dimethylformamide

2: 60 percent

3: 60 percent / hydrogen / 10percent Pd/CaCO₃

4: pyridine / CH₂Cl₂

With pyridine; hydrogen; potassium carbonate; Lindlar's catalyst; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)81938-9

Reference yield:

methyl-6,6-dibromopenicillanate (24138-27-0) → (2S,5R,6S)-3,3-Dimethyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester (76431-34-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent

2: 60 percent / hydrogen / 10percent Pd/CaCO₃

3: pyridine / CH₂Cl₂

With pyridine; hydrogen; Lindlar's catalyst; In dichloromethane;

DOI:10.1016/S0040-4039(01)81938-9

upstream raw materials:

methyl (3S,5R,6S)-6-<(R)-1-hydroxyethyl>penicillanate

2,2,2-Trichloroethyl chloroformate

methyl 6-α-bromo-6-β-<(1R)-hydroxyethyl>penicillanate

6,6-dibromopenicillanic acid

Downstream raw materials:

Carbonic acid (R)-1-((2R,3S)-2-ethylsulfanylthiocarbonylsulfanyl-4-oxo-azetidin-3-yl)-ethyl ester 2,2,2-trichloro-ethyl ester

{(2R,3S)-2-Ethylsulfanylthiocarbonylsulfanyl-4-oxo-3-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

methyl (2α,3β(R*))-2-chloro-α,4-dioxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate

methyl (2α,3β(R*))-2-chloro-α-(isopropylidene)-4-oxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate