4348-74-7

Upstream product

• 65-71-4 thymin 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 127791-68-8 1,4-anhydro-5-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(trimethylsilyl)-D-erythro-pent-1-enitol 
• 127761-84-6 (1R,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-trimethylsilanyloxy-2,6-dioxa-bicyclo[3.1.0]hexane 
• 80393-99-3 1-(2,3,5-Tri-O-benzoyl-α-D-arabinofuranosyl)-5-methyluracil 

Downstream Products

• 127761-89-1 1-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)thymine 
• 917376-47-7 1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}thymine 
• 917376-49-9 N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine 
• 917376-39-7 1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl}thymine 
• 917376-55-7 1-{5-O-(4-monomethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}thymine 
• 917376-63-7 1-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}thymine 
• 917376-41-1 N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl}cytosine 
• 917376-57-9 N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{5-O-(4-monomethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine 
• 917376-65-9 N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine 
• 1039628-51-7 1-(5'-O-benzoyl-α-D-arabinofuranosyl)thymine 

Relevant academic research and scientific papers

Nucleotides. LXXIV* synthesis of α-D-arabino-oligonucleotides

□ 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

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