Journal article
Synthesis of nucleoside epoxyphosphonates
Tetrahedron, Vol.52(36), pp.11695-11704
1996
DOI: 10.1016/0040-4020(96)00684-9
Abstract
Reaction of two regioisomeric uridine derivatives, 1-[3-(diethoxyphosphinyl)-5-O-trityl-β-D-xylofuranosyl]uracil ( 4) and 1-[2-(diethoxyphosphinyl)-5-O-trityl-β-D-arabinofuranosyl]uracil ( 13), with triflyl chloride and 4-pyrrolidinopyridine (4-PDP) results in formation of the corresponding nucleoside epoxyphosphonates. This transformation is immediately useful for confirming the trans relationship of the 2′- and 3′-hydroxyl groups in the geminal hydroxyphosphonates 3 and 12, and provides access to two new families of nucleoside derivatives that may be of interest for their synthetic utility and biological properties. Treatment of ribose-derived geminal hydroxyphosphonates with triflyl chloride and 4-pyrrolidinopyridine results in formation of the corresponding nucleoside epoxyphosphonates.
Details
- Title: Subtitle
- Synthesis of nucleoside epoxyphosphonates
- Creators
- Wenkui Lan McEldoonDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Tetrahedron, Vol.52(36), pp.11695-11704
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/0040-4020(96)00684-9
- ISSN
- 0040-4020
- eISSN
- 1464-5416
- Language
- English
- Date published
- 1996
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9983985923002771
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