Uridine → Uridine

Participants

Reaction Steps

In contrast to the oximation of aldehydes with 5a, its reaction with cholesten-3-one (7) and dansyl chloride gave, as expected, the permanent uridine 2′-conjugates 8 and 19, respectively. These conjugates were both found stable to TBAF/THF under the conditions used for the conversion of 6a-d, 10, 12, 14, and 16 to uridine or cytidine. Indeed, treatment of 19 with 0.5 M TBAF in THF for 72 h at 55° C. produced uridine to the extent of less than 1%, as determined by RP-HPLC analysis of the reaction products.

Provenance & Evidence