title: Efficient reversed-phase purification of a hydrophobic reaction product following Mitsunobu-mediated glycosylation.
abstract: The Mitsunobu reaction was used to attach tetra-O-benzyl-D-glucopyranose to a monoindolylmaleimide, providing a key intermediate in the total synthesis of indolocarbazole topoisomerase I poisons. Using normal-phase silica gel chromatography, purification of the glycosylated product normally required multiple columns, resulting in poor recovered yields. Reversed-phase chromatography was used successfully to purify this highly hydrophobic material, rapidly and in high yield.
authors.affiliation: MediChem Research, Inc., Woodridge, IL 60517, USA.
authors.forename: Mani S
authors.initials: MS
authors.lastname: Iyer
authors.forename: Martin
authors.initials: M
authors.lastname: Palomo
authors.forename: Kevin M
authors.initials: KM
authors.lastname: Schilling
authors.forename: Yongping
authors.initials: Y
authors.lastname: Xie
authors.forename: Leo
authors.initials: L
authors.lastname: Formanski
authors.forename: David E
authors.initials: DE
authors.lastname: Zembower
mesh_terms: D002227:Carbazoles / Q000737:chemistry; D002853:Chromatography, Liquid; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry; D006031:Glycosylation; D007211:Indoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D059004:Topoisomerase I Inhibitors
chemical_list: D002227:Carbazoles; D004791:Enzyme Inhibitors; D007211:Indoles; D059004:Topoisomerase I Inhibitors; D005947:Glucose