161001-99-6

Basic information

• Product Name: Adenosine, N-methyl-N-[[2-(4-nitrophenyl)ethoxy]carbonyl]-
• CAS NO: 161001-99-6
• Molecular Formula: C20H22N6O8
• Molecular Weight: 474.43
• Mol File: 161001-99-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Adenosine, N-methyl-N-[[2-(4-nitrophenyl)ethoxy]carbonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine, N-methyl-N-[[2-(4-nitrophenyl)ethoxy]carbonyl]-(161001-99-6)
• EPA Substance Registry System: Adenosine, N-methyl-N-[[2-(4-nitrophenyl)ethoxy]carbonyl]-(161001-99-6)

Safety Data

• Hazardous Substances Data: 161001-99-6(Hazardous Substances Data)

Upstream product

• 161001-98-5 2',3',5'-tri-O-acetyl-N⁶-methyl-N⁶-(phenyloxycarbonyl)adenosine 
• 161002-00-2 N⁶-methyl-N⁶-(phenyloxycarbonyl)adenosine 
• 161001-95-2 2-(4-nitrophenyl)ethyl 2H-tetrazole-2-carboxylate 
• 56787-20-3 2',3',5'-tri-O-acetyl-N⁶-methyl-adenosine 
• 88091-68-3 2-(4-nitrophenyl)ethoxycarbonyl chloride 
• 1867-73-8 N⁶-methyladenosine 
• 88091-70-7 1-methyl-3-[2-(4-nitrophenyl)ethoxycarbonyl]imidazolium chloride 
• 186581-53-3 diazomethane 
• 88121-73-7 N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 161001-94-1 2',3',5'-tri-O-acetyl-N⁶-methyl-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 

Downstream Products

• 644990-28-3 5'-O-{{2-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}ethoxy}carbonyl}-N⁶-methyl-N⁶-{[2-(4-mitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 
• 644990-26-1 N⁶-methyl-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine 
• 644990-32-9 N⁶-methyl-N⁶-{[2-(4-nitropheyl)ethoxy]carbonyl}-2'-O-(tetrahydro-4-methoxy-2H-pyran-4-yl)adenosine 
• 644990-25-0 N⁶-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine 
• 1867-73-8 N⁶-methyladenosine 

Relevant articles and documents

Nucleotides: Part LXXII. Synthesis of N-methylated ribonucleosides for RNA synthesis

The synthesis of various N-methylated nucleosides (m6A, m 3C, m4C, m3U) is described. These minor nucleosides can be obtained by simple methylation with diazomethane of [2-(4-nitrophenyl)ethoxy]carbonyl(npeoc)-protected nucleosides. These methylated compounds are easily further derivatized to fit into the scheme of the [2-(dansyl)ethoxy]carbonyl (dnseoc) approach for RNA synthesis (dansyl = [5-(dimethylamino)naphthalen-1-yl]sulfonyl). Various oligoribonucleotides containing N6-methyladenosine were synthesized, underlining the usefulness of the dnseoc approach, especially for the synthesis of natural tRNA-derived oligoribonucleotide sequences.

Nucleosides. Part LVI. Aminolysis of carbamates of adenosine and cytidine

The 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) group, introduced 1984 as protecting group for exocyclic amino functions of nucleic-acid bases, reacts with amines under mild conditions to urea derivatives. Treatment of 2',5'-di-O-acetyl-N6-[2-(4-nitrophenyl)ethoxycarbonyl]cordycepin (3) with NH3/MeOH overnight at room temperature affords cordycepin (4) and N6-carbamoylcordycepin (5). Preliminary investigations towards the elucidation of the reaction mechanism indicate that the aminolysis proceeds via an addition-elimination or an isocyanate mechanism, depending on the reaction conditions. The phenoxycarbonyl (phoc) group at N6 or N4 was chosen to study the mild conversion of carbamates with aromatic amines into ureas of adenosine and cytidine, respectively.