SYNTHESIS OF 2,3'-ANHYDRO-2'-DEOXYURIDINES AND 2',3'-DIDEHYDRO-2',3'-DIDEOXYURIDINES USING POLYMER-SUPPORTED FLUORIDE

Authors
LARSEN E KOFOED T PEDERSEN EB
Citation
E. Larsen et al., SYNTHESIS OF 2,3'-ANHYDRO-2'-DEOXYURIDINES AND 2',3'-DIDEHYDRO-2',3'-DIDEOXYURIDINES USING POLYMER-SUPPORTED FLUORIDE, Synthesis, (9), 1995, pp. 1121
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
9
Year of publication
1995
Database
ISI
SICI code
0039-7881(1995):9<1121:SO2A2>2.0.ZU;2-1
Abstract
Reaction of methyl luenesulfonyl-alpha,beta-D-erythro-pentofuranoside (2) with silylated uracils 3 using trimethylsilyl trifluoromethanesulf onate (TMS triflate) as catalyst afforded after crystallization in Et( 2)O the corresponding beta-nucleosides 4. Reaction of 4 with tetrabuty lammonium fluoride (TBAF) or Amberlyst A-26 resin (F--form) in THF at room temperature or at reflux gave the corresponding deprotected 2,3'- anhydro-2'-deoxyuridines 6 and 2',3'-didehydro-2',3'-dideoxyuridines 7 , respectively.