112237-60-2

Upstream product

• 73-03-0 cordycepin 
• 88091-70-7 1-methyl-3-[2-(4-nitrophenyl)ethoxycarbonyl]imidazolium chloride 
• 161001-78-1 2',5'-di-O-acetyl-3'-deoxy-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 71196-28-6 ((2S,4R,5R)-4-acetoxy-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl acetate 

Downstream Products

• 115222-31-6 N⁶-<2-(p-nitrophenyl)ethoxycarbonyl>-3'deoxyadenosine 2',5'-bis(bis<2-(p-nitrophenyl)ethyl> phosphate) 
• 177084-28-5 Carbonic acid (2S,4R,5R)-4-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 2-(4-nitro-phenyl)-ethyl ester 
• 201855-51-8 (9-{(2R,3R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid 2-(4-nitro-phenyl)-ethyl ester 
• 220867-50-5 3'-deoxy-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-5'-O-<(p-toluyl)sulfonyl>adenosine 
• 97776-94-8 3'-deoxy-N⁶,2'-O-bis[2-(p-nitrophenyl)ethoxicarbonyl]adenosine 
• 97776-96-0 3'-deoxy-N⁶-<2-(p-nitrophenyl)ethoxicarbonyl>adenosine 2'-<2,5-dichlorophenyl 2-(p-nitrophenyl)ethyl phosphate> 
• 97776-93-7 3'-deoxy-5'-O-(monomethoxytrityl)-N⁶-<2-(p-nitrophenyl)ethoxycarbonyl>adenosine 2'-<2,5-dichlorphenyl 2-(p-nitrophenyl)ethyl phosphate> 
• 10385-57-6 cordycepin N¹-oxide 
• 177084-44-5 3'-deoxy-N⁶,5'-O-bis<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 2'-<(2RS)-2,3-bis(hexadecanoyloxy)-propyl 2-(4-nitrophenyl)ethyl phosphate> 
• 177084-45-6 3'-deoxy-N⁶,5'-O-bis<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 2'-<(2RS)-2,3-bis(tetradecanoyloxy)-propyl 2-(4-nitrophenyl)ethyl phosphate> 
• 177084-46-7 3'-deoxy-N⁶,5'-O-bis<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 2'-<(2RS)-2,3-bis(hexadecyloxy)propyl 2-(4-nitrophenyl)ethyl phosphate> 
• 179676-36-9 3'-deoxy-2'-O-{[2-(ergocalciferyloxycarbonyl)ethyl]carbonyl}-N⁶,5'-O-bis-[2-(4-nitrophenyl)ethoxycarbonyl]adenosine 
• 179676-37-0 Succinic acid (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyl ester (2R,3R,5S)-2-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-5-[2-(4-nitro-phenyl)-ethoxycarbonyloxymethyl]-tetrahydro-furan-3-yl ester 
• 179676-60-9 Succinic acid mono-{(2R,3R,5S)-2-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-5-[2-(4-nitro-phenyl)-ethoxycarbonyloxymethyl]-tetrahydro-furan-3-yl} ester 

Relevant academic research and scientific papers

38. Nucleotides: Part XLVI. The synthesis of phospholipid conjugates of antivirally active nucleosides by the improved phosphoramidite methodology

The application of the improved phosphoramidite strategy for the synthesis of oligonucleotides using β-eliminating protecting groups to phospholipid chemistry offers the possibility to synthesize phospholipid conjugates of AZT (6) and cordycepin. The synthesis of 3′-azido-3′-deoxythymidine (6) was achieved by a new isolation procedure without chromatographic purification steps in an overall yield of 50%. Protected cordycepin (=3′-deoxyadenosine) derivatives, the N6,2′-bis[2-(4-nitrophenyl)ethoxycarbonyl]cordycepin (12) and the N6,5′-bis[2-(4-nitrophenyl)ethoxycarbonyl]cordycepin (13) were prepared by known methods and direct acylation of N6-[2-(4-nitrophenyl)ethoxycarbonyl]cordycepin (9), respectively. These protected nucleosides and the 3′-azido-3′-deoxythymidine (6) reacted with newly synthesized and properly characterized lipid-phosphoramidites 21-25, catalyzed by 1H-tetrazole, to the corresponding nucleoside-phospholipid conjugates 26-38 in high yield. The deprotection was accomplished via β-elimination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in aprotic solvents to give analytically pure nucleoside-phospholipid diesters 39-51 as triethylammonium or sodium salts. The newly synthesized compounds were characterized by elemental analyses and UV and 1H-NMR spectra.

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.

Nucleotides. Part XXVII. BisPhosphorochloridate, a New Versatile Phosphorilating Agent in Nucleotide Chemistry

A new, versatile phosphorilating agent, bis phosphorochloridate (3), has been prepared and is used for 3'- and/or 5'-phosphorylations of nucleotides.The resulting bis phosphotriesters are versatile synthons