Pirlimycin hydrochloride, U-57930E, -Drug Synthesis Database

【结构式】

【药物名称】Pirlimycin hydrochloride, U-57930E

【化学名称】Methyl 7-chloro-6,7,8-trideoxy-6-[[(cis-4-ethyl-2-piperidinyl)carbonyl]amino]-1-thio-L-threo-alpha-D-galacto-octopyranoside hydrochloride hydrate
　　　　　　cis-4-Ethyl-L-pipecolic acid amide of 7-deoxy-7-(S)-chloromethylthiolincosamide hydrochloride hydrate

【CA登记号】79548-73-5 (free base), 77495-92-2 (monohydrate)

【分子式】C₁₇H₃₄Cl₂N₂O₆S

【分子量】465.44033

【开发单位】Pfizer (Originator)

【药理作用】Antibiotics, ANTIINFECTIVE THERAPY

合成路线1

The condensation of 4-ethylpyridine-2-carboxylic acid (I) with methyl-6-amino-7-chloro-6,7,8-trideoxy-1-thio-L-threo-alpha-D-galacto-octopyranoside (II) by means of isobutyl chloroformate (A) and triethylamine in acetonitrile gives the corresponding amide (III), which is then hydrogenated with H2 over PtO2 in methanol - water - HCl.

参考文献中间体

【1】 Hillier, K.; Serradell, M.N.; Blancafort, P.; Castaner, J.; Pirlimycin hydrochloride. Drugs Fut 1983, 8, 4, 338.
【2】 Birkenmeyer, R.D. (Pharmacia Corp.); Novel antibiotics, their preparation and their use. BE 0886301 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	13423	1-[(Chlorocarbonyl)oxy]-2-methylpropane; Isobutyl chloroformate;isobutyl carbonochloridate	543-27-1	C₅H₉ClO₂	详情	详情
(I)	36053	4-ethyl-2-pyridinecarboxylic acid		C₈H₉NO₂	详情	详情
(II)	36054	(2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-(methylsulfanyl)tetrahydro-2H-pyran-3,4,5-triol		C₉H₁₈ClNO₄S	详情	详情
(III)	36055	N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)tetrahydro-2H-pyran-2-yl]propyl]-4-ethyl-2-pyridinecarboxamide		C₁₇H₂₅ClN₂O₅S	详情	详情

Extended Information