GW-587270

Chemical Name: [1R-(1alpha,3abeta,4alpha,4abeta,7beta,7aalpha,8abeta)]-8a-[4-[2-(Fluoromethyl)-2-propenyl]-6(R)-methylmorpholin-2(R)-yloxymethyl]-4-formyl-3-isopropyl-7-methyl-1,3a,4,4a,5,6,7,7a,8,8a-decahydro-1,4-methano-s-indacene-3a-carboxylic acid
CAS No. 250244-24-7 (potassium salt)
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Oxidative cleavage of 6-deoxy-beta-D-mannopyranosyl sordaricin (I) using sodium periodate furnished dialdehyde (II).Subsequent reductive amination of dialdehyde (II) gave rise to the morpholino derivative (III).Acidic hydrolysis of the ethylene ketal function of (III) provided aldehyde (IV).The carboxylic group was then protected as the benzhydryl ester (V) using diphenyl diazomethane.2-Methylene-1,3-propanediol (VI) was converted to mono-tosylate (VII) by treatment with p-toluenesulfonyl chloride in the presence of dibutyltin oxide and N-methylimidazole.Subsequent hydroxyl group fluorination of (VII) by means of diethylaminosulfur trifluoride provided 2-(fluoromethyl)propenyl tosylate (VIII).Alkylation of the morpholine N of (V) with tosylate (VIII) gave adduct (IX).The benzhydryl ester of (IX) was finally cleaved to the title carboxylic acid by treatment with trifluoroacetic acid.