Efficient reversed-phase purification of a hydrophobic reaction product following Mitsunobu-mediated glycosylation.
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.
Iyer
Mani S
MS
MediChem Research, Inc., Woodridge, IL 60517, USA.
Palomo
Martin
M
Schilling
Kevin M
KM
Xie
Yongping
Y
Formanski
Leo
L
Zembower
David E
DE
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
D002227:Carbazoles; D004791:Enzyme Inhibitors; D007211:Indoles; D059004:Topoisomerase I Inhibitors; D005947:Glucose