Desacetylcephalothin

Base Information

• Chemical Name: Desacetylcephalothin
• CAS No.: 5935-65-9
• Molecular Formula: C14H14 N2 O5 S2
• Molecular Weight: 354.408
• European Community (EC) Number: 227-690-8
• DSSTox Substance ID: DTXSID70974769
• Nikkaji Number: J223.900K
• Wikidata: Q76009672
• Mol file: 5935-65-9.mol

Synonyms:deacetylcephalothin;desacetylcephalothin;desacetylcephalothin, (6R-(6alpha,7beta))-isomer;desacetylcephalothin, monopotassium salt, (6R-trans)-isomer;desacetylcephalothin, monosodium salt, (6R-trans)-isomer

Chemical Property of Desacetylcephalothin

Chemical Property:

• PSA: 160.48000
• Density: 1.8g/cm³
• LogP: 0.35030
• Storage Temp.: -20°C Freezer
• Solubility.: Dioxane (Very Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 354.03441390
• Heavy Atom Count: 23
• Complexity: 580

Purity/Quality:

99% ^*data from raw suppliers

DES-ACETYL CEPHALOTHIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CS3)C(=O)O)CO
• Isomeric SMILES: C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CS3)C(=O)O)CO
• Uses: Deacetylcephalothin (Cefalotin EP Impurity B) is an intermediate and the free acid analogue of Deacetylcephalothin Sodium Salt (D198210), which is an impurity in the synthesis of Cefalonium (C236800) and an analog of Cephalothin (C261150) a first-generation cephalosporin antibiotic used as a long-acting intramammary cerate for infusion of dairy cows.

Technology Process of Desacetylcephalothin

There total 8 articles about Desacetylcephalothin 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: 85.8%

cephalothin (153-61-7) → Desacetylcephalothin (5935-65-9)

Guidance literature:

With ammonium hydroxide; immobilized deacetylase; at 20 - 30 ℃; for 0.5h; pH=6.5 - 7.5; pH-value; Enzymatic reaction;

Reference yield: 84.47%

2-thienylacetic acid chloride (39098-97-0) + (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7) → Desacetylcephalothin (5935-65-9)

Guidance literature:

(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; With triethylamine; In dichloromethane; at 0 - 5 ℃; for 1h;

2-thienylacetic acid chloride; In dichloromethane; at 0 - 25 ℃; for 2h; Reagent/catalyst;

Reference yield: 80.0%

sodium cephalothin (58-71-9) → Desacetylcephalothin (5935-65-9)

Guidance literature:

sodium cephalothin; With sodium hydroxide; In water; at -20 - -10 ℃; for 0.0375h;

With hydrogenchloride; In water; pH=1.5; Further stages.; cooling;

DOI:10.3390/molecules13040841

upstream raw materials:

sodium cephalothin

7-Aminocephalosporanic acid

methyl 2-thiopheneacetate

cephalothin

Downstream raw materials:

cefoxitin lactone

3-hydroxymethyl-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester

3-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester

(6R,7R)-3-[(4-formamido-1-pyridinyl)methyl]-8-oxo-7-[(2-acetylamino-2-yl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate