23589-13-1Relevant articles and documents
Anomers of Tubercidin Derivatives with 2-Methylthio and N4-(Δ2-Isopentenyl) Residues
Seela, Frank,Bussmann, Werner
, p. 1972 - 1980 (2007/10/02)
Starting with the chloronucleosides 3a and 4a the anomers 1 and 2 of 2-(methylthio)tubercidin were prepared.They are desulfurized to tubercidin (3c) and its α-anomer 4c.Desulfurization of the N4-(Δ2-isopentenyl) compounds 3b and 4b yields 3d and 4d; due to hydrogenation the by-products 3e and 4e are formed.Isopentylation of tubercidin followed by Dimroth rearrangement also gives N4-(Δ2-isopentenyl)tubercidin (3d).From the 1J(C,H) coupling constants of the glyconic moiety the sequence of the 13C signals of the α-anomer 2 was deduced.The 3J(C-6,1'-H) couplings of tubercidins gave the torsion angle χ which is found to be in the anti region.