Synthesis and separation of diastereomers of uridine 2',3'-cyclic boranophosphate.
The first boron-containing 2',3'-cyclic phosphate-modified analogue, uridine 2',3'-cyclic boranophosphate (2',3'-cyclic-UMPB), was synthesized. 5'-O-Protected uridine was cyclophosphorylated by diphenyl H-phosphonate to yield uridine 2',3'-cyclic H-phosphonate, which upon silylation followed by boronation and subsequent acid treatment gave 2',3'-cyclic-UMPB in high yield. The two diastereomers of 2',3'-cyclic-UMPB were separated by HPLC. An alternative method for synthesis of uridine 2',3'-cyclic phosphorothioate (2',3'-cyclic-UMPS) via H-phosphonate was also described.
Department of Chemistry, Gross Chemical Laboratory, Duke University, Durham, NC 27708, USA.
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D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D008968:Molecular Conformation; D015394:Molecular Structure; D012260:Ribonucleases / Q000037:antagonists & inhibitors; D013237:Stereoisomerism; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification
D001896:Boron Compounds; C432543:uridine-2',3'-cyclic boranophosphate; D012260:Ribonucleases; D014529:Uridine