Thienamycin

Base Information

• Chemical Name: Thienamycin
• CAS No.: 59995-64-1
• Molecular Formula: C11H16 N2 O4 S
• Molecular Weight: 272.325
• UNII: EWR2GDB37H,WMW5I5964P
• DSSTox Substance ID: DTXSID10975412
• Nikkaji Number: J20.130H
• Wikipedia: Thienamycin
• Wikidata: Q3524791
• Metabolomics Workbench ID: 68783
• ChEMBL ID: CHEMBL278773
• Mol file: 59995-64-1.mol

Synonyms:epithienamycin;thienamycin;thienamycin, ((5alpha,6alpha(S*))-(+-))-isomer;thienamycin, (5R-(5alpha,6alpha(R*)))-isomer;thienamycin, (5R-(5alpha,6alpha(S*)))-isomer;thienamycin, (5R-(5alpha,6beta(S*)))-isomer;tienamycin

Chemical Property of Thienamycin

Chemical Property:

• Vapor Pressure: 1.02E-12mmHg at 25°C
• Refractive Index: 1.662
• Boiling Point: 514°C at 760 mmHg
• PKA: 4.20±0.40(Predicted)
• Flash Point: 264.7°C
• PSA: 129.16000
• Density: 1.5g/cm³
• LogP: 0.22420
• Storage Temp.: Hygroscopic, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 272.08307817
• Heavy Atom Count: 18
• Complexity: 423

Purity/Quality:

98%Min ^*data from raw suppliers

Thienamycin(>80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN)O
• Isomeric SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN)O
• Uses: Thienamycin is one of the most potent naturally produced antibiotics known thus far. It has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes.

Technology Process of Thienamycin

There total 35 articles about Thienamycin 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:

(S)-1-(tert-Butyl-dimethyl-silanyl)-4-(2-trimethylsilanyl-[1,3]dithian-2-ylmethyl)-azetidin-2-one (75321-01-6) → thienamycin (59995-64-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 82 percent Turnov_. / LDA / tetrahydrofuran / -78 °C

2: K-Selectride, KI / diethyl ether / 25 °C

3: 93 percent / HgCl₂, HgO / methanol; H₂O / Heating

4: 76 percent / hydrogen peroxide / methanol; H₂O

5: tetrahydrofuran / Ambient temperature

6: 86 percent / tetrahydrofuran / Ambient temperature

7: HCl / methanol

8: 90 percent / p-carboxybenzenesulfonyl azide, Et₃N / acetonitrile / 0 - 20 °C

9: rhodium(II) acetate / benzene / 80 °C

10: DMAP, i-Pr₂NEt / acetonitrile / 0 °C

11: 70 percent / i-Pr₂NEt / acetonitrile / -5 °C

12: H₂ / Pd/C / 2068.6 Torr

With rhodium(II) acetate; hydrogenchloride; dmap; p-carboxybenzenesulfonyl azide; hydrogen; dihydrogen peroxide; potassium tri-sec-butyl-borohydride; triethylamine; N-ethyl-N,N-diisopropylamine; potassium iodide; mercury dichloride; mercury(II) oxide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; acetonitrile; benzene;

DOI:10.1021/ja00539a040

Reference yield:

p-nitrobenzyl (5R,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate (64067-13-6) → thienamycin (59995-64-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; under 2068.6 Torr;

DOI:10.1021/ja00539a040

Reference yield:

4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (75363-99-4) → thienamycin (59995-64-1)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP, i-Pr₂NEt / acetonitrile / 0 °C

2: 70 percent / i-Pr₂NEt / acetonitrile / -5 °C

3: H₂ / Pd/C / 2068.6 Torr

With dmap; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In acetonitrile;

DOI:10.1021/ja00539a040

upstream raw materials:

p-nitrobenzyl (5R,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate

formamidine acetic acid

imipenem

ethane-1,2-dithiol

Downstream raw materials:

1-methyl-2-pyridone

C₂₃H₂₅N₃O₄S

N-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin lithium salt

p-nitrobenzyl (5R,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate

Refernces

• 1、 Smith,Dezeny,Douglas. "Stability and kinetics of degradation of imipenem in aqueous solution". . p. 732 - 740. Retrieved 2007/10/02.
• 2、 -. "Salts of amino-beta-lactamic acids and process for the preparation thereof". . . Retrieved 2008/06/13.