80393-99-3

Basic information

• Product Name: 1-(2,3,5-Tri-O-benzoyl-α-D-arabinofuranosyl)-5-methyluracil
• Synonyms: 1-(2,3,5-Tri-O-benzoyl-α-D-arabinofuranosyl)-5-methyluracil
• CAS NO: 80393-99-3
• Molecular Weight: 570.555
• Mol File: 80393-99-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-(2,3,5-Tri-O-benzoyl-α-D-arabinofuranosyl)-5-methyluracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3,5-Tri-O-benzoyl-α-D-arabinofuranosyl)-5-methyluracil(80393-99-3)
• EPA Substance Registry System: 1-(2,3,5-Tri-O-benzoyl-α-D-arabinofuranosyl)-5-methyluracil(80393-99-3)

Safety Data

• Hazardous Substances Data: 80393-99-3(Hazardous Substances Data)

Upstream product

• 7473-42-9 methyl tri-O-benzoyl-α-D-arabinofuranoside 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 57236-69-8 (3S,4R,5R)-2-acetoxy-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 
• 65-71-4 thymin 

Downstream Products

• 4348-74-7 1-(α-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione 
• 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 

Relevant articles and documents

Propargyl 1,2-orthoesters for a catalytic and stereoselective synthesis of pyrimidine nucleosides

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.

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.