298699-71-5

Upstream product

• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 50-89-5 thymidine 
• 64987-77-5 2-(2-nitrophenyl)propanol 
• 612-22-6 2-nitro(ethylbenzene) 
• 702642-19-1 2-ethyl-1-iodo-3-nitrobenzene 
• 13985-60-9 2-ethyl-1,3,5-trinitrobenzene 
• 339571-01-6 carbonic acid 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-(2-nitro-phenyl)-propyl ester 
• 154187-40-3 2-(2-nitrophenyl)propyl carbonochloridate 
• 702642-17-9 1-bromo-2-ethyl-3-nitrobenzene 
• 702642-25-9 4-ethyl-3,5-dinitrobenzeneamine 
• 90007-09-3 2-ethyl-3-nitrobenzeneamine 
• 13985-56-3 2-ethyl-1,3-dinitrobenzene 
• 179691-31-7 2-(2-nitrophenyl)propyl chloroformate 

Downstream Products

• 60249-97-0 1-(1-methylethenyl)-2-nitrobenzene 
• 50-89-5 thymidine 

Relevant academic research and scientific papers

Carbonic ester type photosensitive reagent and preparation method thereof as well as preparation method of 5'-photolabile dN

The invention relates to a carbonic ester type photosensitive reagent and a preparation method thereof as well as a preparation method of 5'-photolabile dN. The structural formula of the carbonic ester type photosensitive reagent is shown in the specification, wherein X is -OX', imidazolyl or substituted imidazolyl. The preparation method of 5'-photolabile dN comprises the following steps: preparing a crude product of 5'-photolabile dN from 2'-deoxynucleoside and 2-o-nitrobenzene-1-propyl carbonic ester type photosensitive reagent and triethylamine; and purifying the crude product to obtain the 5'-photolabile dN. According to the preparation method of 5'-photolabile dN, the selectivity is improved by 3.4 times on average, the purifying process is simplified, the yield is increased, the production cost is greatly reduced, and the use of virulent diphosgene is avoided.

New Types of Very Efficient Photolabile Protecting Groups Based upon the [2-(2-Nitrophenyl)propoxy]carbonyl (NPPOC) Moiety

Based upon the photolabile [2-(2-nitrophenyl)propoxy]carbonyl group (NPPOC), a large number of modified 2-(2-nitrophenyl)propanol derivatives substituted at the phenyl ring (see 23-34 and 57-76) as well as at the side-chain (see 85-92 and 95-98) were synthesized to improve the photoreactivity of this new type of photolabile entity. The phenyl moiety was also exchanged by the naphthalenyl group (see 102, 103, 105, 108, 110, 113, and 114), the thienyl substituent (see 115, 117, 118, and 120), and the benzothienyl substituent (see 121). The 2-(2-nitroaryl- and heteroaryl) propanols were converted with diphosgene into the corresponding carbonochloridates, which reacted subsequently with thymidine to the thymidine 5′-(protected carbonates) 123-178 as the main reaction products. In several cases, the corresponding 3′-carbonates and 3′,5′ -dicarbonates 179-212 were also isolated and characterized. Photolysis studies under standardized conditions (see Table) indicated that the rate of photocleavage varies in a broad range depending on the substituents. So far, the thymidine 5′-[2-(5-halo-2-nitrophenyl)propyl carbonates] 127-129, 5′-[2-(nitro[1,1′-biphenyl]3-yl)propyl carbonates] 136-139, 5′-{2-[2-nitro-5-(thianthren-1-yl)phenyl]propyl carbonate} (140), 5′-[2-(5-naphthalenyl-2-nitrophenyl)propyl carbonates] 141 and 142, and 5′-[2-(2-nitro-5-thienylphenyl)propyl carbonates] 143 and 144 showed the best properties regarding fast and uniform deprotection. Since the nucleobases of 213-215 do not influence the photocleavage features, in general, the new type of photolabile building blocks allows in form of their 3′ -phosphoramidites the photolithographic formation of high-quality biochips.

3'-nitrophenylpropyloxycarbonyl (NPPOC) protecting groups for high-fidelity automated 5' --> 3' photochemical DNA synthesis.

[structure: see text]. The most powerful DNA microarrays would be prepared by photolithography with free 3'-ends that could be processed enzymatically. A photoremovable group that could be removed in quantitative yield would ensure high purity of the synt

Synthesis of photolabile 5′-o-phosphoramidites for the photolithographic production of microarrays of inversely oriented oligonucleotides

The photolabile 3′-O-{[2-(2-nitrophenyl)propoxy]carbonyl}-protected 5′-phosphoramidites (16-18) were synthesized (see Scheme) for an alternative mode of light-directed production of oligonucleotide arrays. Because of the characteristics of these monomeric

New photolabile protecting groups in nucleoside and nucleotide chemistry - Synthesis, cleavage mechanisms and applications

New photolabile protecting groups have been found in the 2-(2- nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. β-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced β-elimination process is proposed.