Synthesis and conformational analysis of a novel type of spin labelled bicyclonucleoside based on a tetrahydrofurano[2,3-c]pyrrolidine sugar skeleton.
Bicyclonucleosides bearing a 5-deoxy-5-N-hydroxyamino-3,N5-(1,1-ethano)-beta-D-furanosyl sugar moiety (15-18) have been prepared by glycosidation of the corresponding bicyclosugars obtained via an intramolecular reverse Cope elimination. The configuration of the asymmetric carbon of the 1,1-ethano bridge is the most important factor directing the conformation of the N-hydroxypyrrolidine ring and its invertomers ratio as shown by variable temperature H NMR experiments.
Department of Organic Pharmaceutical Chemistry, University of Geneva, Switzerland.
J M
JM
Tronchet
L
L
Brenas
F
F
Barbalat-Rey
M
M
Zsély
M
M
Geoffroy
D002241:Carbohydrates / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013113:Spin Labels; D013941:Thymine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D002241:Carbohydrates; D005663:Furans; D011759:Pyrrolidines; D013113:Spin Labels; D013941:Thymine; D014529:Uridine