Title: Synthesis of α-l-Threose Nucleoside Phosphonates via Regioselective Sugar Protection
Authors: Dumbre, Shrinivas
Jang, Miyeon
Herdewijn, Piet # ×
Issue Date: Jul-2013
Publisher: American Chemical Society
Series Title: Journal of Organic Chemistry vol:78 issue:14 pages:7137-44
Article number: 10.1021/jo400907g
Abstract: A new synthesis route to α-l-threose nucleoside phosphonates via 2-O and 3-O selectively protected l-threose is developed. The key intermediates 2-O-benzoyl-l-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-l-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and 3'-C-ethynyl l-threose 3'-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new l-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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