title: Synthesis and NMR assignment of the two diastereomers of 8,6'-cyclo-2',6'-dideoxyadenosine.
abstract: We herein present the first synthesis and characterization of the two C5' diastereomers of 8,6'-cyclo-2',6'-dideoxyadenosine. Starting from commercially available 2'-deoxyadenosine, the target cyclonucleosides were synthesized in 11 linear steps. Following a zinc-mediated cyclization reaction to form the seven-membered ring, the stereochemistry of the newly formed chiral center was established using two-dimensional NOESY NMR experiments.
authors: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors: Han
authors: H
authors: Yueh
authors: Ayan
authors: A
authors: Pal
authors: Kenneth
authors: K
authors: Chang
authors: Mark K
authors: MK
authors: Schlegel
authors: Larry W
authors: LW
authors: McLaughlin
mesh_terms: D003500:Cyclization; D003839:Deoxyadenosines / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D003839:Deoxyadenosines