203200-32-2

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 203200-31-1 1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylselanyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 

Downstream Products

• 267243-95-8 1-[3-O-(allyldimethylsilyl)-2-deoxy-5-O-(dimethoxytrityl)-4-C-(phenylseleno)-α-L-threo-pento-1,4-furanosyl]thymine 
• 203200-36-6 [2-(2,2,2-Trifluoro-acetylamino)-ethyl]-carbamic acid 2-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester 
• 246022-21-9 5'-O-(4,4'-dimethoxytrityl)-4'αC-vinylthymidine 
• 267244-05-3 5'-O-(dimethoxytrityl)-4'-C-[3-(N-trifluoroacetyl)aminopropyl]thymidine 
• 267243-99-2 4'-C-(3-azidopropyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine 
• 267244-04-2 5'-O-(dimethoxytrityl)-4'-C-[2-(N-trifluoroacetyl)aminoethyl]thymidine 
• 267243-97-0 3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)-4'-C-(3-hydroxypropyl)thymidine 
• 267244-01-9 4'-C-(3-azidopropyl)-5'-O-(dimethoxytrityl)thymidine 
• 267244-00-8 4'-C-(2-azidoethyl)-5'-O-(dimethoxytrityl)thymidine 
• 267243-98-1 4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine 

Relevant academic research and scientific papers

Synthesis of oligodeoxynucleotides containing 4'-C-aminoalkylthymidines and their thermal stability and nuclease-resistance properties

To find the nuclease-resistant oligodeoxynucleotides (ODNs) with natural phosphodiester linkages, we designed and synthesized ODNs containing 4'-C- aminoalkylthymidines (1-4). We found that the ODNs containing 1, 2, 3 or 4 were more resistant to nucleolyt

Nucleosides and Nucleotides. 174. Synthesis of Oligodeoxynucleotides Containing 4′-C-[2-[[N-(2-Aminoethyl)carbamoyl]oxy]ethyl]thymidine and Their Thermal Stability and Nuclease-Resistance Properties

The synthesis and properties of oligodeoxynucleotides (ODNs) containing 4′-C-[2-[[N-(2-arninoethyl)-carbamoyl]oxy]ethyl]thymidine (3) are described. 4′α-(2-Hydroxyethyl)thymidine (4), which is a precursor for phosphoramidite 5, was synthesized using a newly developed intramolecular radical cyclization reaction at the 4′-position of thymidine derivative 7. The radical reaction of 4′β-(phenylseleno)-3′-O-(dimethylvinylsilyl)thymidine derivative 7, which was prepared from thymidine in several steps, with Bu3SnH and AIBN, followed by Tamao oxidation, gave either 4′α-(2-hydroxyethyl) derivative 6 or 4′α-(1-hydroxy ethyl) derivative 13, respectively. With a low Bu3-SnH concentration, the reaction gave 6, via 6-endo-radical-cyclized product 11, as a sole product in 87% yield. The reaction of 7 in the presence of excess Bu3SnH gave 13 in 75% yield, via 5-exo-cyclized product 12, as a diastereomeric mixture. The 4′α-(2-hydroxyethyl) derivative 6 was then converted into a 4′-C-[2-[[N-(2-aminoethyl)carbamoyl]oxy]ethyl]thymidine derivative 14, which was phosphitylated to give phosphoramidite 5 in 72% yield. In this study, 3 was incorporated into a nonadecamer, d[CTGGCTCAGCTCGTCTCAT]-3′, and a heptadecamer, d[CTCGTACCATTCCGCTC]3′, instead of T at various positions. ODNs containing 3 were more resistant to nucleolytic hydrolysis by both snake venom phosphodiesterase (a 3′-exonuclease) and DNase I (an endonuclease) than unmodified parent ODNs, although ODNs containing 3 only slightly destabilized duplex formation with both complementary DNA and RNA strands. Furthermore, the duplex formed by an ODN containing 3 and its complementary RNA was a good substrate for Escherichia coli RNase H.