title: Determination of etoposide phosphate intermediates by gradient liquid chromatography using postcolumn derivatization with cuprammonium hydroxide.
abstract: Allyl 4,6-O-ethylidene-beta-D-glucopyranoside is an intermediate used in the synthesis of etoposide phosphate, a water-soluble derivative of the antineoplastic drug etoposide. In this paper, a method for the determination of allyl 4,6-O-ethylidene-beta-D-glucopyranoside and related glucopyranosides is described. Samples are analyzed by gradient high-performance liquid chromatography using postcolumn derivatization with cuprammonium hydroxide. The method is used to monitor the ethylidenation reaction of allyl beta-D-glucopyranoside with acetal to form allyl 4,6-O-ethylidene-beta-D-glucopyranoside. Samples are chromatographed on an octadecyl-bonded phase column with aqueous acetonitrile. Triethylamine is added to the mobile phase to accelerate mutarotation and suppress anomeric separations. The column effluent is mixed via a postcolumn tee with cuprammonium hydroxide and monitored with ultraviolet detection at 310 nm.
authors.affiliation: Bristol-Myers Squibb Company, Technical Operations, Syracuse, NY 13221-4755, USA. vincent.demperio@bms.com
authors.forename: Vincent L
authors.initials: VL
authors.lastname: Demperio
mesh_terms: D000970:Antineoplastic Agents / Q000032:analysis*; D002853:Chromatography, Liquid / Q000379:methods*; D005047:Etoposide / Q000031:analogs & derivatives* / Q000032:analysis*; D006878:Hydroxides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000032:analysis*; D011355:Prodrugs / Q000032:analysis*; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000970:Antineoplastic Agents; D006878:Hydroxides; D009943:Organophosphorus Compounds; D011355:Prodrugs; C468555:cuprammonium hydroxide; C061400:etoposide phosphate; D005047:Etoposide