218152-30-8

Upstream product

• 100-27-6 2-(4-nitrophenyl)ethanol 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 3056-33-5 2,9-diacetylguanine 
• 917376-69-3 N²,N⁹-diacetyl-O⁶-2-(4-nitrophenyl)ethylguanine 

Downstream Products

• 344414-08-0 N-tert-butoxycarbonyl-[N-2(N²-acetyl-O⁶-p-nitrophenylethylguanine-9-yl)ethyl]glycine methyl ether 
• 213902-34-2 O⁶-2-(4-nitrophenyl)ethylguanine 
• 316353-09-0 (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-(3-{N²-acetyl-O⁶-[2-(4-nitrophenyl)ethyl]-9-guaninyl}propyl)oxazolidin-5-one 
• 917376-87-5 O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine 
• 917376-86-4 O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4-monomethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine 
• 917474-26-1 O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine 
• 917376-75-1 O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)guanine 
• 917376-79-5 O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl]guanine 
• 917376-84-2 O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine 
• 917376-74-0 O⁶-[2-(4-nitrophenyl)ethyl]-9-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)guanine 
• 917376-76-2 O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(α-D-arabinofuranosyl)guanine 

Relevant academic research and scientific papers

N2-acetyl-O6-(2-(p-nitrophenyl)ethyl)guanine: A convenient building block for the synthesis of 9-substituted guanine derivatives

Readily accessible N2-acetyl-O6-(2-(p-nitrophenyl)ethyl)guanine can undergo Mitsunobu reactions with either a primary or secondary alcohol to generate guanine derivatives. X-ray data indicates that only the desired 9- subsituted derivatives of guanine are formed.

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.

Synthesis of N-Boc and N-Fmoc dipeptoids with nucleobase residues as peptoid nucleic acid monomers

The synthesis of Boc and Fmoc protected peptoid nucleic acid monomers bearing thymine (4a, 4b), adenine (6a, 6b) or guanine (7a, 7b) on the side chain is described. These nucleobases were attached to the amino group of glycine via an ethylene linkage using the Mitsunobu reaction, except cytosine, which was attached using alkylation. After deprotection, these amino acids have been used for synthesizing N-Boc and N-Fmoc dipeptoids.