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.
Haikal
Abdellfattah Z
AZ
Department of Chemistry, Faculty of Science, University of United Arab Emirates, PO Box 17551, Alain, United Arab Emirates.
El Ashry
El Sayed H
el SH
Banoub
Joseph
J
D013058:Mass Spectrometry; D015394:Molecular Structure; D010793:Phthalazines / Q000138:chemical synthesis* / Q000737:chemistry*
D010793:Phthalazines; C043388:phthalazine