THE SYNTHESIS OF 2,3-DIDEOXY-2-FLUORO-3-C-METHYLPENTOSE-CONTAINING NUCLEOSIDES VIA [3,3]-SIGMATROPIC REARRANGEMENTS

Authors
ARAKI K YUN WQ OTOOLE J TOSCANO PJ WELCH JT
Citation
K. Araki et al., THE SYNTHESIS OF 2,3-DIDEOXY-2-FLUORO-3-C-METHYLPENTOSE-CONTAINING NUCLEOSIDES VIA [3,3]-SIGMATROPIC REARRANGEMENTS, Carbohydrate research, 249(1), 1993, pp. 139-161
Citations number
94
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Carbohydrate research → ACNP
ISSN journal
00086215
Volume
249
Issue
1
Year of publication
1993
Pages
139 - 161
Database
ISI
SICI code
0008-6215(1993)249:1<139:TSO2N>2.0.ZU;2-0
Abstract
[3,3]-Sigmatropic rearrangement of in situ-formed [0,0]-silyl ketene a cetals of butenyl fluoroacetates was used as the key step in the synth esis of racemic 2,3-dideoxy-2-fluoro-3-C-methylpentofuranoses. The pro duct pentofuranoses were transformed further into pyrimidine and purin e nucleosides. The conformations of the synthetic carbohydrates were c onfirmed by single-crystal X-ray diffraction studies and indicated tha t previous structural assignments made by NMR were in error.