carbapenem MM22383

Base Information

• Chemical Name: carbapenem MM22383
• CAS No.: 65322-98-7
• Molecular Formula: C13H16N2O5S
• Molecular Weight: 312.34
• DSSTox Substance ID: DTXSID40628444
• Wikidata: Q27126387
• Metabolomics Workbench ID: 60333
• Mol file: 65322-98-7.mol

Synonyms:carbapenem MM22383;65322-98-7;MM22383;CHEBI:58998;(5R,6S)-3-[(E)-2-acetamidoethenyl]sulfanyl-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;(5R,6S)-3-{[(E)-2-acetamidovinyl]sulfanyl}-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;Epithienamycin D;(5R,6S)-2-{[(E)-2-acetamidovinyl]sulfanyl}-6-[(1S)-1-hydroxyethyl]-2,3-didehydro-1-carbapenam-3-carboxylic acid;Epitope ID:119423;SCHEMBL11078340;DTXSID40628444;C17398;Q27126387

Chemical Property of carbapenem MM22383

Chemical Property:

• PSA: 135.73000
• LogP: 1.01280
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 312.07799279
• Heavy Atom Count: 21
• Complexity: 557

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C2CC(=C(N2C1=O)C(=O)O)SC=CNC(=O)C)O
• Isomeric SMILES: C[C@@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)S/C=C/NC(=O)C)O

Technology Process of carbapenem MM22383

There total 9 articles about carbapenem MM22383 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: 62.5%

p-nitrobenzyl (+/-)-cis-3-<(E)-2-acetamidovinylthio>-6β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (74819-56-0,74843-45-1,77449-49-1,84278-70-6,90694-16-9) → (+/-)-epithienamycin B (65322-98-7,65376-20-7,68738-07-8,77448-05-6,79056-58-9)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; platinum(IV) oxide; In tetrahydrofuran; for 1h; Pressure (range begins): 40 ; Ambient temperature;

DOI:10.1039/P19810002282

Reference yield:

(+/-)-4β-carboxymethyl-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (76335-76-7,77448-00-1,79299-25-5,90581-13-8,150284-14-3) → (+/-)-epithienamycin B (65322-98-7,65376-20-7,68738-07-8,77448-05-6,79056-58-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) N,N'-carbonyldiimidazole

2: p-toluenesulphonyl azide, triethylamine

3: rhodium diacetate

4: 4-dimethylaminopyridine, diisopropylethylamine / acetonitrile

5: NaI / acetonitrile / 0 °C

6: NaHCO₃, H₂ / Adams catalyst / tetrahydrofuran; H₂O / 2068.6 Torr

With rhodium(II) acetate; dmap; 4-toluenesulfonyl azide; hydrogen; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; sodium iodide; platinum(IV) oxide; In tetrahydrofuran; water; acetonitrile;

Reference yield:

(+/-)-4β-formylmethyl-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (77447-99-5) → (+/-)-epithienamycin B (65322-98-7,65376-20-7,68738-07-8,77448-05-6,79056-58-9)

Guidance literature:

Multi-step reaction with 7 steps

1: Jones reagent

2: 1.) N,N'-carbonyldiimidazole

3: p-toluenesulphonyl azide, triethylamine

4: rhodium diacetate

5: 4-dimethylaminopyridine, diisopropylethylamine / acetonitrile

6: NaI / acetonitrile / 0 °C

7: NaHCO₃, H₂ / Adams catalyst / tetrahydrofuran; H₂O / 2068.6 Torr

With rhodium(II) acetate; dmap; 4-toluenesulfonyl azide; jones reagent; hydrogen; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; sodium iodide; platinum(IV) oxide; In tetrahydrofuran; water; acetonitrile;

upstream raw materials:

p-nitrobenzyl (+/-)-cis-3-<(E)-2-acetamidovinylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

(+/-)-4β-carboxymethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

(5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(+/-)-4β-formylmethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one