NF-115
Chemical Name: Octyl 2-acetamido-2-deoxy-6-O-[3-hydroxy-2,2-bis(hydroxymethyl)propyl]-alpha-D-glucopyranoside
CAS No. 368870-53-5
项目整合开发状态: Preclinical
项目研究机构: CSIC (Originator), Hospital Universitario Puerta de Hierro (Originator)
合成路线:Condensation of N-acetyl-D-glucosamine (I) with n-octanol in the presence of boron trifluoride etherate affords the alpha-glycoside (II).Selective protection of the primary hydroxyl group of (II) with trityl chloride yields the O-trityl derivative (III),which is subsequently reacted with benzyl bromide to furnish the dibenzyl ether (IV).Then,O-trityl group cleavage under acidic conditions gives rise to the primary alcohol (V).(1,2)
合成路线:Pentaerythritol (VI) is condensed with anisaldehyde dimethylacetal (VII) to produce the pentaerythritol mono-benzylidene acetal (VIII).Subsequent reaction of diol (VIII) with sulfuryl diimidazole leads to the cyclic sulfate (IX) (1).Alkylation of alcohol (V) with sulfate (IX) in the presence of NaH gives rise to the ether adduct (X).Hydrogenolysis of the benzyl and benzylidene groups of (X) over Pd/C affords (XI).Finally,acid hydrolysis of the sulfate group in (XI) furnishes the target compound.(1,2)
📌 参考资料/链接：
参考文献标题:Glycosides of N-acetyl-6-O-[2,2,-bis(hydroxymethyl)-3-hydroxypropyl]-D-glucosamine,method for the obtention thereof and their uses in the treatment of brain tumors
文献作者:Nieto Sampedro,M.; Bernabe Pajares,M.; Fernandez-Mayoralas Alvarez,A.; Vaquero Crespo,J.; Zurita Castillo,M.(CSIC (Consejo Superior de Investigaciones Cient韋icas); Hospital Universitario Puerta de Hierro)
参考来源:ES 2164013; WO 0179243
📄 详细内容
合成路线:Condensation of N-acetyl-D-glucosamine (I) with n-octanol in the presence of boron trifluoride etherate affords the alpha-glycoside (II).Selective protection of the primary hydroxyl group of (II) with trityl chloride yields the O-trityl derivative (III),which is subsequently reacted with benzyl bromide to furnish the dibenzyl ether (IV).Then,O-trityl group cleavage under acidic conditions gives rise to the primary alcohol (V).(1,2)
合成路线:Pentaerythritol (VI) is condensed with anisaldehyde dimethylacetal (VII) to produce the pentaerythritol mono-benzylidene acetal (VIII).Subsequent reaction of diol (VIII) with sulfuryl diimidazole leads to the cyclic sulfate (IX) (1).Alkylation of alcohol (V) with sulfate (IX) in the presence of NaH gives rise to the ether adduct (X).Hydrogenolysis of the benzyl and benzylidene groups of (X) over Pd/C affords (XI).Finally,acid hydrolysis of the sulfate group in (XI) furnishes the target compound.(1,2)
参考文献标题:Central neural tumor destruction by controlled release of a synthetic glycoside dispersed in a biodegradable polymeric matrix
文献作者:Fern醤dez-Mayoralas,A.; De la Figuera,N.; Zurita,M.; Vaquero,J.; Abraham,G.A.; San Rom醤,J.; Nieto-Sampedro,M.
参考来源:J Med Chem 2003,46(8),1286