Selective phosphitylation of the primary hydroxyl group in unprotected carbohydrates and nucleosides.
[reaction: see text] Carbohydrates and nucleosides containing a phosphate at the less-hindered primary hydroxyl group are often prepared using a protection/deprotection strategy. Herein we report that the phosphoramidite method can be used to selectively incorporate phosphorus at the primary hydroxyl group of O-unprotected carbohydrates and nucleosides; in situ oxidation of the resulting phosphite triester yields the phosphate triester.
Graham
S M
SM
Department of Chemistry, St. John's University, Jamaica, New York 11439, USA. grahams@stjohns.edu
Pope
S C
SC
D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D017665:Hydroxyl Radical; D007202:Indicators and Reagents; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D017905:Phosphites / Q000138:chemical synthesis*; D010766:Phosphorylation
D002241:Carbohydrates; D007202:Indicators and Reagents; D009705:Nucleosides; D017905:Phosphites; D017665:Hydroxyl Radical