Synthesis and structural characterization of 1-(D-glycosyloxy)phthalazines.
Coupling of the trimethylsilyl derivative of (2H)phthalazin-1-one with 1,2,3,4,6-penta-O-acetyl-alpha-D-glucopyranose and 1,2,3,4,6-penta-O-acetyl-alpha-D-galactopyranose in the presence of stannic chloride gave the respective glycosides, 2-(per-O-acetyl-D-glycosyloxy)phthalazines, which upon deacetylation gave the respective unprotected analogues. Under the same conditions 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose gave 1-(2,3,5-tri-O-acetyl-alpha-D-ribofuranosyloxy)phthalazine. Electrospray mass spectrometry aided the structural characterization of this series of 1-(D-glycosylyloxy)phthalazines. Low energy collisionally-induced dissociation tandem mass spectrometry of the protonated molecules confirmed the MS fragmentation routes and the structural identities of this novel series of glycosides.
Department of Chemistry, Faculty of Science, University of United Arab Emirates, PO Box 17551, Alain, United Arab Emirates.
Abdellfattah Z
AZ
Haikal
El Sayed H
el SH
El Ashry
Joseph
J
Banoub
D013058:Mass Spectrometry; D015394:Molecular Structure; D010793:Phthalazines / Q000138:chemical synthesis* / Q000737:chemistry*
D010793:Phthalazines; C043388:phthalazine