Deacetoxycephalosporin C

Base Information

• Chemical Name: Deacetoxycephalosporin C
• CAS No.: 26924-74-3
• Molecular Formula: C14H19 N3 O6 S
• Molecular Weight: 357.387
• DSSTox Substance ID: DTXSID00181424
• Nikkaji Number: J92.761I
• Wikidata: Q27102924
• Metabolomics Workbench ID: 51201
• Mol file: 26924-74-3.mol

Synonyms:deacetoxycephalosporin C;deacetoxycephalosporin C, (6R-(6alpha,7beta))-isomer;deacetoxycephalosporin C, disodium salt;deacetoxycephalosporin C, monosodium salt;desacetoxycephalosporin C

Chemical Property of Deacetoxycephalosporin C

Chemical Property:

• Vapor Pressure: 4.1E-27mmHg at 25°C
• Boiling Point: 786.3°Cat760mmHg
• Flash Point: 429.3°C
• PSA: 178.82000
• Density: 1.54g/cm³
• LogP: 0.80560
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 357.09945651
• Heavy Atom Count: 24
• Complexity: 620

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N2C(C(C2=O)NC(=O)CCCC(C(=O)O)N)SC1)C(=O)O
• Isomeric SMILES: CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CCC[C@H](C(=O)O)N)SC1)C(=O)O

Technology Process of Deacetoxycephalosporin C

There total 3 articles about Deacetoxycephalosporin C 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: 100.0%

penicillin N (525-94-0) → deacethoxycephalosporin C (26924-74-3)

Guidance literature:

With ring expansion enzyme from Cephalosporium CO₇₂₈; oxygen; α-ketoglutarate; iron(II) sulfate; ascorbic acid; diothiothreitol; at 30 ℃; pH=7.5;

DOI:10.1039/c39870000374

Reference yield:

α-ketoglutaric acid (328-50-7) + penicillin N (525-94-0) → succinic acid (110-15-6) + deacethoxycephalosporin C (26924-74-3)

Guidance literature:

With deacetoxycephalosporin C synthase; oxygen; iron(II); Enzymatic reaction;

DOI:10.1021/bi500086p

Reference yield:

penicillin N (525-94-0) → deacethoxycephalosporin C (26924-74-3) + (2R,3S,6R,7R)-1-aza-3-methyl-3-hydroxy-7-<(5R)-5-amino-5-carboxypentanamido>-8-oxo-5-thiazbicyclo<4.2.0>octane-2-carboxylate (79495-65-1) + desacetyl cephalosporin C (1476-46-6)

Guidance literature:

In water; N,N-dimethyl-formamide; for 2h; deacetoxy/deacetylcephalosporin C synthase, α-ketoglutarate, L-ascorbate, dithiothreitol, Fe(SO4)2, (NH4)2SO4, pH 7.4;

DOI:10.1016/S0040-4020(01)80725-0

upstream raw materials:

penicillin N

α-ketoglutaric acid

Refernces

• 1、 Baldwin,Adlington,Crouch,Schofield,Turner,Aplin. "Cephalosporin biosynthesis: A branched pathway sensitive to an isotope effect". . p. 9881 - 9900. Retrieved 2007/10/02.
• 2、 Baldwin, Jack E.,Adlington, Robert M.,Crabbe, M. James,Knight, Graham,Nomoto, Takashi,et al.. "THE ENZYMATIC RING EXPANSION OF PENICILLINS TO CEPHALOSPORINS: SIDE CHAIN SPECIFICITY". . p. 3009 - 3014. Retrieved 2007/10/02.