Cefamandole, Mandokef, Kefadol, Kefandol, Mandol, -Drug Synthesis Database

【结构式】

【药物名称】Cefamandole, Mandokef, Kefadol, Kefandol, Mandol

【化学名称】(6R,7R)-7-[2(R)-hydroxy-2-phenylacetamido]-3-(1-methyl-1H-tetraazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

【CA登记号】34444-01-4

【分子式】C₁₈H₁₈N₆O₅S₂

【分子量】462.50936

【开发单位】Lilly (Originator), Dista (Not Determined)

【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, Cephalosporins

合成路线1

The formylation of 7-aminocephalosporanic acid (I) by the usual techniques produces 7-formamidocephalosporanic acid (II), which is then treated with the sodium salt of 1-methyl-1H-tetrazole-5-thiol (III) to yield 7-formamido-3-(1-methyl-1H-tetrazol-5-ylthio)methyl-3-cephem-4-carboxylic acid (IV). The resulting product (IV) is deformylated affording 7-amino-3-(1-methyl-1H-tetrazol-5-ylthio)methyl-3-cephem-4-carboxylic acid (V), which is finally acylated with anhydro-O-carboxymandelic acid (VI) using the usual techniques.

参考文献中间体

【1】 Castañer, J.; Cefamandole. Drugs Fut 1977, 2, 10, 646.
【2】 Tensmeyer, L.G. (Eli Lilly and Company); Cefamandole derivatives. US 3947415 .
【3】 Tensmeyer, L.G. (Eli Lilly and Company); Cefamandole derivatives. US 3947414 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	22747	(6R,7R)-3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₀H₁₂N₂O₅S	详情	详情
(II)	40146	(6R,7R)-3-[(acetoxy)methyl]-7-(formylamino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₁H₁₂N₂O₆S	详情	详情
(III)	40147	sodium 1-methyl-1H-1,2,3,4-tetraazole-5-thiolate		C₂H₃N₄NaS	详情	详情
(IV)	40148	(6R,7R)-7-(formylamino)-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₁H₁₂N₆O₄S₂	详情	详情
(V)	32663	(6R,7R)-7-amino-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	24209-38-9	C₁₀H₁₂N₆O₃S₂	详情	详情
(VI)	40149	(5R)-5-phenyl-1,3-dioxolane-2,4-dione		C₉H₆O₄	详情	详情

Extended Information