189216-59-9

Upstream product

• 179691-31-7 2-(2-nitrophenyl)propyl chloroformate 
• 50-89-5 thymidine 
• 64987-77-5 2-(2-nitrophenyl)propanol 
• 702642-19-1 2-ethyl-1-iodo-3-nitrobenzene 
• 13985-56-3 2-ethyl-1,3-dinitrobenzene 
• 13985-60-9 2-ethyl-1,3,5-trinitrobenzene 
• 612-22-6 2-nitro(ethylbenzene) 
• 90007-09-3 2-ethyl-3-nitrobenzeneamine 
• 702642-25-9 4-ethyl-3,5-dinitrobenzeneamine 
• 702642-17-9 1-bromo-2-ethyl-3-nitrobenzene 

Downstream Products

• 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.

New photolabile protecting groups of the 2-(2- nitrophenyl)ethoxycarbonyl-and the 2-(2-nitrophenyl)ethylsulfonyl-type for the oligonucleotide synthesis

New photolabile blocking groups have been synthesized and introduced into the 5'-OH position of thymidine. The 5'-O-protected thymidines were irradiated at 365 nm under identical conditions and the half-lives and thymidine yields were determined to investigate the influence of different substituents in the two corresponding series.

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.

Nucleoside derivatives with photolabile protective groups

The invention relates to nucleoside derivatives having photolabile protective groups of the general formula (I) STR1 in which R1 =H, NO2, CN, OCH3, halogen or alkyl or alkoxyalkyl having 1 to 4 C atoms R2 =H, OCH3 R3 =H, F, Cl, Br, NO2 R4 =H, halogen, OCH3, or an alkyl radical having 1 to 4 C atoms R5 =H or a usual functional group for preparing oligonucleotides R6 =H, OH, halogen or XR8, where X=O or S and R8 represents a protective group usual in nucleotide chemistry, B=adenine, cytosine, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazolcarboxamid-1-yl, or 5-amino-4-imidazolcarboxamid-3-yl, where in the case of B=adenine, cytosine or guanine, the primary amino function optionally exhibits a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.