Cephalonium lactone

Base Information

• Chemical Name: Cephalonium lactone
• CAS No.: 10590-10-0
• Molecular Formula: C₁₄H₁₂N₂O₄S₂
• Molecular Weight: 336.392
• Mol file: 10590-10-0.mol

Synonyms:2-Thiopheneacetamide,N-(1,4,5a,6-tetrahydro-1,7-dioxo-3H,7H-azeto[2,1-b]furo[3,4-d][1,3]thiazin-6-yl)-,(5aR-trans)- (8CI); 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-(hydroxymethyl)-8-oxo-7-[2-(2-thienyl)acetamido]-, g-lactone (7CI);3H,7H-Azeto[2,1-b]furo[3,4-d][1,3]thiazine, 2-thiopheneacetamide deriv.;Deacetylcephalothin lactone

Chemical Property of Cephalonium lactone

Chemical Property:

• PSA: 129.25000
• LogP: 0.83020
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

DeacetylcephalothinLactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Deacetylcephalothin Lactone (Cefalotin EP Impurity D) is an impurity in the synthesis of Cefalonium (C236800), a first-generation cephalosporin antibiotic used as a long-acting intramammary cerate for infusion of dairy cows.

Technology Process of Cephalonium lactone

There total 17 articles about Cephalonium lactone 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: 95.7%

Desacetylcephalothin (5935-65-9) → cefoxitin lactone (10590-10-0)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 25 - 35 ℃; for 2h; Reagent/catalyst; Solvent; Temperature;

Reference yield: 62.0%

methyl 7β-(2-thienylacetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate (19702-56-8) → cefoxitin lactone (10590-10-0)

Guidance literature:

With potassium carbonate; In methanol; water; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2020.127515

Reference yield:

cephalothin (153-61-7) → cefoxitin lactone (10590-10-0)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jm00323a023

upstream raw materials:

cephalothin

Desacetylcephalothin

sodium cephalothin

7-Aminocephalosporanic acid

Refernces

• 1、 Indelicato,Engel,Occolowitz. "Cephalothin: Hydrolysis of the C-3'-acetoxy moiety of a 7-aminocephalosporanic acid; observation of both acyl-oxygen bond cleavage and reversible alkyl-oxygen bond cleavage". . p. 1162 - 1166. Retrieved 1985.
• 2、 Chauvette,Flynn. "Chemistry of cephalosporin antibiotics. V. Amides and esters of cephalothin.". . p. 741 - 745. Retrieved 2007/10/06.