112237-60-2Relevant articles and documents
38. Nucleotides: Part XLVI. The synthesis of phospholipid conjugates of antivirally active nucleosides by the improved phosphoramidite methodology
Sigmund, Harald,Pfleiderer, Wolfgang
, p. 426 - 438 (2007/10/03)
The application of the improved phosphoramidite strategy for the synthesis of oligonucleotides using β-eliminating protecting groups to phospholipid chemistry offers the possibility to synthesize phospholipid conjugates of AZT (6) and cordycepin. The synthesis of 3′-azido-3′-deoxythymidine (6) was achieved by a new isolation procedure without chromatographic purification steps in an overall yield of 50%. Protected cordycepin (=3′-deoxyadenosine) derivatives, the N6,2′-bis[2-(4-nitrophenyl)ethoxycarbonyl]cordycepin (12) and the N6,5′-bis[2-(4-nitrophenyl)ethoxycarbonyl]cordycepin (13) were prepared by known methods and direct acylation of N6-[2-(4-nitrophenyl)ethoxycarbonyl]cordycepin (9), respectively. These protected nucleosides and the 3′-azido-3′-deoxythymidine (6) reacted with newly synthesized and properly characterized lipid-phosphoramidites 21-25, catalyzed by 1H-tetrazole, to the corresponding nucleoside-phospholipid conjugates 26-38 in high yield. The deprotection was accomplished via β-elimination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in aprotic solvents to give analytically pure nucleoside-phospholipid diesters 39-51 as triethylammonium or sodium salts. The newly synthesized compounds were characterized by elemental analyses and UV and 1H-NMR spectra.
Nucleotides. Part XXVII. BisPhosphorochloridate, a New Versatile Phosphorilating Agent in Nucleotide Chemistry
Himmelsbach, Frank,Charubala, Ramamurthy,Pfleiderer, Wolfgang
, p. 1286 - 1295 (2007/10/02)
A new, versatile phosphorilating agent, bis phosphorochloridate (3), has been prepared and is used for 3'- and/or 5'-phosphorylations of nucleotides.The resulting bis phosphotriesters are versatile synthons