Cephemimycin

Base Information

• Chemical Name: Cephemimycin
• CAS No.: 34279-51-1
• Deprecated CAS: 37226-22-5,40958-02-9
• Molecular Formula: C₁₆H₂₂N₄O₉S
• Molecular Weight: 446.438
• UNII: XA69811MWE
• DSSTox Substance ID: DTXSID10955835
• Nikkaji Number: J17.435A
• Wikidata: Q27106127
• Metabolomics Workbench ID: 53058
• Mol file: 34279-51-1.mol

Synonyms:A 16886B;A-16886B;A16886B;cephamycin C;cephamycin C sodium;cephamycin C, (6R)-isomer;cephamycin C, (6R-(6alpha,7alpha,7(R*)))-isomer;cephamycin C, (6R-(6alpha,7alpha,7(S*)))-isomer;cephamycin C, monosodium salt;cephamycin C, sodium salt

Chemical Property of Cephemimycin

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 244.19000
• Density: g/cm³
• LogP: 0.24140
• XLogP3: -4.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 446.11074947
• Heavy Atom Count: 30
• Complexity: 802

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1(C2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CCCC(C(=O)O)N
• Isomeric SMILES: CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CCC[C@H](C(=O)O)N

Technology Process of Cephemimycin

There total 1 articles about Cephemimycin 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:

→ (6R)-7t-((R)-5-amino-5-carboxy-pentanoylamino)-3-carbamoyloxymethyl-7c-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (32178-84-0,34279-51-1,38429-35-5,39212-31-2,64162-09-0)

Guidance literature:

Streptomyces Lactamdurans (MA 2908);

Reference yield:

(6R)-7t-((R)-5-amino-5-carboxy-pentanoylamino)-3-carbamoyloxymethyl-7c-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2 ene-2-carboxylic acid (34279-51-1) → (6R)-7t-((R)-5-benzhydryloxycarbonyl-5-tert-butoxycarbonylamino-pentanoylamino)-3-carbamoyloxymethyl-7c-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (35607-76-2)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. K₂HPO₄, 4-dimethylaminopyridine / acetone

2: ethyl acetate

With dmap; dipotassium hydrogenphosphate; In ethyl acetate; acetone;

DOI:10.1248/cpb.24.2629

Reference yield:

(6R)-7t-((R)-5-amino-5-carboxy-pentanoylamino)-3-carbamoyloxymethyl-7c-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2 ene-2-carboxylic acid (34279-51-1) → (6R)-7t-((R)-5-benzhydryloxycarbonyl-5-tert-butoxycarbonylamino-pentanoylamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (57793-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. K₂HPO₄, 4-dimethylaminopyridine / acetone

2: (i) aq. NaHCO₃, (ii) /BRN= 779235/, Et₂O

With dmap; dipotassium hydrogenphosphate; In acetone;

DOI:10.1248/cpb.24.2629

Downstream raw materials:

(6R)-7t-((R)-5-benzhydryloxycarbonyl-5-tert-butoxycarbonylamino-pentanoylamino)-3-carbamoyloxymethyl-7c-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R)-7t-((R)-5-benzhydryloxycarbonyl-5-tert-butoxycarbonylamino-pentanoylamino)-7c-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester