beta-L-2'-Fd4FC

Chemical Name: 1-(2,3-Dideoxy-2-fluoro-beta-L-glycero-pent-2-enofuranosyl)-5-fluorocytosine
CAS No. 181785-91-1
项目整合开发状态: Biological Testing
项目研究机构: Emory University (Originator), University of Georgia (Originator), Yale University (Originator)
合成路线:L-Glyceraldehyde acetonide (I) was subjected to Horner-Emmons reaction with triethyl alpha-fluorophosphonoacetate (II) in the presence of sodium bis(trimethylsilyl)amide to yield a mixture of Z (III) and E (IV) unsaturated esters.Acidic treatment of this mixture,followed by silylation with tert-butyldimethylsilyl chloride gave the desired fluorobutyrolactone (V) along with the open-chain silylated dihydroxyester (VI),which were separated by column chromatography.Reduction of lactone (V) with DIBAL provided an anomeric mixture of lactols (VIIa-b),which was further acetylated to afford (VIIIa-b).N-Glycosylation of the silylated N(4)-benzoylcytosine (IX) using trimethylsilyl triflate gave rise to the mixture of furanosylcytosines (Xa-b).After chromatographic isolation of the desired beta-anomer,deprotection of the silyl ether by means of tetrabutylammonium fluoride yielded (XI).Finally,ammonolysis of the N-benzoyl group of (XI) furnished the title compound.