108310-92-5

Upstream product

• 100-27-6 2-(4-nitrophenyl)ethanol 
• 69992-10-5 3',5'-di-O-acetyl-2'-deoxyguanosine 
• 961-07-9 2'-Deoxyguanosine 

Downstream Products

• 169049-77-8 3',5'-O-diacetyl-2'-deoxy-2-fluoro-O₆-[2-(4-nitrophenyl)ethyl]inosine 
• 233756-58-6 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-{2-[(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonyl)-amino]-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-3-yl ester 
• 849830-82-6 2-chloro-6-(2-(p-nitrophenyl)ethyloxy)-9-[2'-deoxy-β-D-erythropentofuranosyl]purine diacetate 
• 132183-39-2 2-fluoro-O⁶-(2-(p-nitrophenyl)ethyl)-2'-deoxyinosine 
• 153527-28-7 5'-O-(4,4'-Dimethoxytrityl)-6-O-[2-(4-nitrophenyl)ethyl]-2'-deoxy-2-fluoroinosine 
• 209785-64-8 2-Benzylamino-9-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-1,9-dihydro-purin-6-one 
• 209785-66-0 9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-phenethylamino-1,9-dihydro-purin-6-one 
• 209785-67-1 9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-(3-phenyl-propylamino)-1,9-dihydro-purin-6-one 
• 209785-68-2 9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-[(naphthalen-1-ylmethyl)-amino]-1,9-dihydro-purin-6-one 
• 209785-69-3 9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-[(naphthalen-2-ylmethyl)-amino]-1,9-dihydro-purin-6-one 
• 209785-71-7 2-[(Biphenyl-3-ylmethyl)-amino]-9-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-1,9-dihydro-purin-6-one 
• 209785-70-6 2-[(Biphenyl-4-ylmethyl)-amino]-9-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-1,9-dihydro-purin-6-one 
• 209785-65-9 N²-benzyl-O⁶-(2-(4-nitrophenyl)ethyl)-5′-(4,4′-dimethoxytrityl)-2′-deoxyguanosine 

Relevant academic research and scientific papers

2’-DEOXYGUANOSINE HYBRID COMPOUND CONTAINING PYRROLE AMIDE TETRAMER, METHOD OF PRODUCING THE SAME AND PRODUCTION INTERMEDIATE THEREFOR

It is intended to provide an MGB polyamide hybrid compound which has a function of recognizing a base sequence useful in gene therapy, is efficacious in synthesizing an oligomer and has a high stability. An MGB polyamide hybrid compound represented by the following formula (38) which is characterized by being a pyrrole amide tetramer prepared by introducing a 1-methylpyrrole-2-carbonyl group as a substitute for the N-terminal formyl group in the existing case.

Nucleotides: Part LXXI. A new type of labelling of nucleosides and nucleotides

A new labelling technique attaching fluorescein via a carbamoyl linker directly to the amino groups of the nucleobases was developed. The amino groups were first converted to the phenoxycarbonyl derivatives (→ 10, 15, 19, 58), which reacted under mild conditions with 5-aminofluorescein to give the corresponding N-[(fluorescein-5-ylamino)carbonyl] derivatives (→ 11-14, 16, 17, 20, 59, 60). The introduction of the 5-aminofluorescein residue into properly protected adenylyl-adenosine dimers (→ 39, 40) and trimer (→ 50) worked well, and final deprotection of these uniformly blocked precursors led on treatment with DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), in one step to dimer 41 and trimer 51. Synthesis of an appropriately protected monomeric phosphoramidite building block (→ 75) was more difficult, since introduction of the 2-(4-nitrophenyl) ethyl residue into the fluorescein moiety in 59 led mainly to trisubstitution to give 61 including the urea function. Formation of the adenylyl dimer 66 and trimer 67 proceeded in the usual manner by phosphoramidite chemistry; however, deprotection of 67 with DBU was incomplete since the O-alkyl group at the urea moiety was found to be very stable. Finally, the appropriate phosphoramidite building block 75 could be synthesized by the sequence 59 → 72 → 73 → 74 → 75. The phosphoramidite 75 was used for the synthesis of dimer 77 and trimer 79 by solution chemistry, as well as for that of various oligonucleotides by the machine-aided approach on solid support carrying the fluorophore at different positions of the chain (→ 84-87). The attachment of the fluorescein fluorophor via a short carbamoyl linker onto the 6-amino group of 2′-deoxyadenosine enables such molecules to function very well in fluorescence-polarization experiments.

New 2-(4-nitrophenyl)ethyl(Npe)- and 2-(4- nitrophenyl)ethoxycarbonyl(Npeoc)protected 2'-deoxyribonucleosides and their 3'-phosphoramidites - Versatile building blocks for oligonucleotide synthesis

A series of new base-protected and 5'-O-(4-monomethoxytrityl)- or 5'-O- (4,4'-dimethoxytrityl)-substituted 3'-(2-cyanoethyl diisopropylphosphoramidites) and 3'-[2-(4-nitrophenyl)ethyl diisopropylphosphoramidites] 52-66 and 67-82, respectively, are prepare

N2- and C8-substituted oligodeoxynucleotides with enhanced thrombin inhibitory activity in vitro and in vivo.

2'-Deoxyguanosine (G) analogues carrying various hydrophobic substituents in the N2 and C8 positions were synthesized and introduced through solid-phase synthesis into 15-mer oligodeoxynucleotide, GGTTGGTGTGGTTGG, which forms a chairlike structure consist

Nucleosides. Part LI. The 2-(4-Nitrophenyl)ethoxycarbonyl (npeoc) and 2-(2,4-Dinitrophenyl)ethoxycarbonyl (dnpeoc) Groups for Protection of Hydroxy Functions in Ribonucleosides and 2'-Deoxyribonucleosides

The common 2'-deoxypyrimidine and -purine nucleosides, thymidine (4), O4-thymidine (17), 2'-deoxy-N4-cytidine (26), 2'-deoxy-N6-adenosine (39), and 2'-deoxy-N2--O6-guanosine (52) were further protected by the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) and the 2-(2,4-dinitrophenyl)ethoxycarbonyl (dnpeoc) group at the OH functions of the sugar moiety to form new partially and fully blocked intermediates for nucleoside and nucleotide syntheses.The corresponding 5'-O-monomethoxytrityl derivatives 5, 18, 30, 40, and 56 were also used as starting material to synthesize some other intermediates which were not obtained by direct acylations.In the ribonucleoside series, the 5'-O-monomethoxytrityl derivatives 14, 36, 49, and 63 reacted with 2-(4-nitrophenyl)ethyl chloroformate (1) to the corresponding 2',3'-bis-carbonates 15, 37, 50, and 64 which were either detritylated to 16, 38, 51, and 65, respectively, or converted by 1,8-diazabicycloundec-7-ene (DBU) treatment to the 2',3'-cyclic carbonates 66-69.The newly synthesized compounds were characterized by elemental analyses and UV and 1H-NMR spectra.