80393-99-3Relevant academic research and scientific papers
Propargyl 1,2-orthoesters for a catalytic and stereoselective synthesis of pyrimidine nucleosides
Rao, Boddu Venkateswara,Manmode, Sujit,Hotha, Srinivas
, p. 1499 - 1505 (2015/02/19)
Pyrimidine nucleosides are synthesized by using propargyl 1,2-orthoesters and Au(III) salt as a catalyst. Strategically positioned 1,2-orthoesters are found to yield only 1,2-trans nucleosides and enable preparation of 2′-OH containing pyrimidine nucleosides. The glycosyl donor employed in this study is stable and easily accessible. The identified high-yielding protocol is mild, diastereoselective, and catalytic.
A procedure for facile synthesis of nucleosides using N, O-Bistrimethyl- silylacetamide in the presence of natural phosphate coated with potassium iodide
Baddi, Laila,Smietana, Michael,Sebti, Said,Vasseur, Jean-Jacques,Lazrek, Hassan B.
experimental part, p. 196 - 199 (2011/07/08)
Several α-D/L-arabino and β-D/L- xylonucleosides were synthesized in good yields under mild conditions by N-glycosylation of 1-O-acetyl D/L- arabino, and xylofuranose, with silylated nucleobases (uracil, thymine and 6- azauracil) in acetonitrile using natural phosphate (NP) coated with potassium iodide in BSA as catalyst.
Nucleotides. LXXIV* synthesis of α-D-arabino-oligonucleotides
Henke, Christoph,Pfleiderer, Wolfgang
, p. 1665 - 1706 (2007/10/03)
□ The 5 α-D-arabinofuranosylnucleosides α-araU (15), α-araT (18), α-araC (22), α-araA (25), and α-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2′-hydroxy group at the sugar moiety were protected by the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) group (37-40) and the amide function in α-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5′-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3′-OH group led to the monomeric building blocks 66-75 as well as the 3′-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-α- arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between α-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-α-D-arabinonucleotide with a complementary oligo-2′-deoxy-β-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-α-arabino- nucleotide synthesis were furthermore demonstrated by the synthesis of the tα-ANAhis a structural analog of the natural tRNAhis of the phage T5. Copyright Taylor & Francis Group, LLC.
A surprising ring opening mechanism in the formation of α-D-arabinofuranosyl nucleosides from 5-substituted uracils
Jorgensen,Pedersen,Nielsen
, p. 1299 - 1306 (2007/10/02)
Reaction of silylated 5-substituted uracil derivatives 6 with methyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside (3) in the presence of trimethylsilyl trifluoromethanesulfonate afforded a mixture of the corresponding 5-substituted 1-(2,3,5-tri-O-benzoyl-α-D
