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

REFERENCES

• Parikh , J. R. , Wolff , M. E. and Burger , A. 1957 . Analogs of nucleotides. II. phosphonate esters of ribose and glucopyranosyl purine derivatives . J. Am. Chem. Soc. , 79 : 2778 – 2781 .
   Web of Science ®Google Scholar
• De Clercq , E. , Holy , A. , Rosenberg , I. , Sakuma , T. , Balzarini , J. and Maudgal , P. C. 1986 . A novel selective broad-spectrum anti-DNA virus agent . Nature , 323 : 464 – 467 .
   PubMed Web of Science ®Google Scholar
• Shaw , B. R. , Sergueev , D. , He , K. , Porter; , K. , Summers , J. , Sergueeva , Z. and Rait , V. 1999 . Boranophosphate backbone: a mimic of phosphodiesters, phosphorothioates, and methylphosphonates . Methods in Enzymology: Antisense Technology , 313 : 226 – 257 .
   Web of Science ®Google Scholar
• Meyer , P. , Schneider , B. , Sarfati , S. , Deville-Bonne , D. , Guerreiro , C. , Boretto , J. , Janin , J. , Veron , M. and Canard , B. 2000 . Structural basis for activation of alpha-boranophosphate nucleotide analogues targeting drug-resistant reverse transcriptase . EMBO J. , 19 : 3520 – 3529 .
   PubMed Web of Science ®Google Scholar
• An , H. , Wang , T. , Maier , M. A. , Manoharan , M. , Ross , B. S. and Cook , P. D. 2001 . Synthesis of novel 3′-C-methylene thymidine and 5-methyluridine/cytidine H-phosphonates and phosphonamidites for new backbone modification of oligonucleotides . J. Org. Chem. , 66 : 2789 – 2801 .
   PubMed Web of Science ®Google Scholar
• Compound 6: 1H NMR (D2O) δ 7.65–7.23 (m, 8H, Ph), 4.12 (m, 1H, H-9), 1.96 (m, 2H, CH2), (+)0.62-(−)0.03 (br, 3H, BH3); 31P NMR (D2O) δ 100.60 (br, 1P); LC-MS m/z 257.0, calcd for C14H14BO2P− (M−): 257.09
   Google Scholar
• Compound 7: 31P NMR (D2O) δ 115.60 (br, 1P, P-α), -9.95 (s, 1P, P-γ), -20.23 (s, 1P, P-β); LC-MS m/z 416.6, calcd for C14H17BO8P3 − (M−): 417.02
   Google Scholar