Short synthesis of octosyl nucleosides.
[reaction: see text] Commercial 1,2:5,6-di-O-isopropylidene-alpha-d-allofuranose was converted to a protected bicyclic octosyl acid thioglycoside donor by a 10-step sequence that features an intramolecular ester enolate alkylation. Glycosylation of N-benzoyladenine and methyl uridine-5-carboxylate followed by deprotection gave the respective nucleosides "octosyl adenine" and octosyl acid A.
Knapp
Spencer
S
Department of Chemistry & Chemical Biology, Rutgers - The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, USA. knapp@rutchem.rutgers.edu
Thakur
Vinay V
VV
Madduru
Machender R
MR
Malolanarasimhan
Krishnan
K
Morriello
Gregori J
GJ
Doss
George A
GA
D000225:Adenine / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*
D009705:Nucleosides; D000225:Adenine