112237-60-2

Basic information

• Product Name: 3'-deoxy-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
• Synonyms: 3'-deoxy-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
• CAS NO: 112237-60-2
• Molecular Weight: 444.404
• Mol File: 112237-60-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3'-deoxy-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-deoxy-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine(112237-60-2)
• EPA Substance Registry System: 3'-deoxy-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine(112237-60-2)

Safety Data

• Hazardous Substances Data: 112237-60-2(Hazardous Substances Data)

Upstream product

• 73-03-0 cordycepin 
• 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 
• 88091-70-7 1-methyl-3-[2-(4-nitrophenyl)ethoxycarbonyl]imidazolium chloride 

Downstream Products

• 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 
• 97776-93-7 3'-deoxy-5'-O-(monomethoxytrityl)-N⁶-<2-(p-nitrophenyl)ethoxycarbonyl>adenosine 2'-<2,5-dichlorphenyl 2-(p-nitrophenyl)ethyl phosphate> 
• 97776-96-0 3'-deoxy-N⁶-<2-(p-nitrophenyl)ethoxicarbonyl>adenosine 2'-<2,5-dichlorophenyl 2-(p-nitrophenyl)ethyl phosphate> 
• 97776-94-8 3'-deoxy-N⁶,2'-O-bis[2-(p-nitrophenyl)ethoxicarbonyl]adenosine 
• 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 
• 201855-52-9 (9-{(2R,3R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid 2-(4-nitro-phenyl)-ethyl ester 
• 220867-55-0 3',5'-dideoxy-5'-(hexadecanoylamino)-N⁶-<<2-(4-nitrophenyl)ethoxycarbonyl>amino>adenosine 2'-O-<2-cyanoethyl diisopropylphosphoramidite> 
• 220867-54-9 3',5'-dideoxy-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>-5'-<<2-(4-nitrophenyl)ethoxycarbonyl>amino>adenosine 2'-O-<2-cyanoethyl diisopropylphosphoramidite> 

Relevant articles and documents

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.

Nucleotides. Part XXVIII. Chemical syntheses of the 2'-5'-cordycepin-trimer core

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