Analogs of Nucleotides. II. Phosphonate Esters of Ribose and Glucopyranosyl Purine Derivatives¹

Synthesis of 9-Fluorenemethyl Boranophosphonodiphosphate Via an H-Phosphonate Approach

“…[1] Since then, numerous synthetic approaches and biological applications have been reported for various nucleoside phosphonates. Potent antiviral activity (HSV, CMV, HBV, HIV) has been associated with phosphonoalkylnucleobases, e.g., 9-[3-hydroxy-2-(phosphonylmethoxy)-propyl]adenine (HPMPA) and 9-[2-(phosphonylmethoxy)ethyl]adenine (PMEA).…”

Nucleoside Phosphonic Acids. I. The Synthesis of 5'-Deoxyuridine 5'-Phosphonic Acids and Derivatives*

“…Preliminary attempts to polymerize 5'-deoxyuridine 5 '-phosphonylphosphate using polynucleotide phosphorylase were unsuccessful. et al, 1957;Holy et al, 1965) and phosphonate (Parikh et al, 1957;Wolff and Burger, 1959;Bannister and Kagan, 1960) group in place of the naturally occurring phosphate group. The synthesis of a nucleoside triphosphate analog has been reported (Myers et al, 1963) which contains a methylene group in place of the terminal pyrophosphate oxygen.…”

Halogen and Nucleoside Derivatives of Acyclic 2-Amino-2-deoxy-D-glucose.1,2 I

“…30-60°) to give a product formulated as 3,4,5,6-tetra-O-acety 1-1 -chloro-1,1,2-trideoxy-l-[(1,1 -dichloroethyl)thio]-2-(2,4-dinitroanilino) -dglucose aldehydrol (IV): yield 0.35 g. (33%); m.p. 152-154°; [a]20d -224 ± 4°( c 1.2, chloroform22); X*®( 5.60 (OAc), 6.10, 6.22, 6.55 (aryl C=C), 7.55 (N02), 13.60, and 14.05 µ (substituted phenyl); X-ray powder diffraction data,21 8.67 s (1), 8.12 m, 6.97 m, 6.28 w, 5.72 m (3), 4.85 s (2), 4.70 vw, 4.51 vw, 4.21 vw, 4.10 w, 3.85 w, 3.69 w; n.m.r. data,21 8.33 (singlet, 3 protons, CH3CC12S-), 7.94 (singlet, 6 protons), 7.85 (singlet, 3 protons), 7.74 (singlet, 3 protons) (3,4,5,6-0Ac), 3.65 (doublet, ,2 = 3.0 c.p.s., 1 proton, H-l), no absorption in the regions 7.0-7.5 and 8.5-9.0.…”