Biomimetic Phosphonylation and Phosphorylation of Glycoses and Deoxynucleosides

In a one-pot reaction with yields of over 80%, phosphonic or phosphoric acids 1 (R1, R2 = H/OH and OH/OH, respectively) react with glucose or thymidine (dimethoxytrityl derivative) as the alcohol, and propylene oxide or epichlorohydrin 2 (X = CH3 and CH2Cl, respectively) as the condensation agent to give the respective alkyl phosphonates and phosphates 4. The biomimetic reaction proceeds presumably via intermediate 3.