50571-26-1

Upstream product

• 102987-83-7 5′-O-(4,4′-dimethoxytrityl)thymidine-3′-O-[2-cyanoethyl]phosphonate 
• 120942-89-4 Phosphorous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester bis-(2,2,2-trifluoro-1-trifluoromethyl-ethyl) ester 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 160056-33-7 Phenyl 5'-O-dimethoxytritylthymidin-3'-yl phosphonate 
• 89849-93-4 5'-O-dimethoxytritylthymidin-3'-yl 3'-O-(1,3-benzodithiol-2-yl)thymidin-5'-yl H-phosphonate 
• 50-89-5 thymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 104655-76-7 5'-O-dimethoxytrityl thymidine 3'-O-phosphorbisdiethylamidite 
• 98796-51-1 5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidine-3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite] 
• 104655-82-5 5'-O-(p,p'-dimethoxytrityl)thymidine 3'-(allyl N,N-diisopropylphosphoramidite) 
• 1000692-08-9 C₃₃H₃₇N₂SPO₈ 
• 157793-52-7 p-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphonate 
• 104684-77-7 C₃₄H₃₇N₂O₉P 

Downstream Products

• 157793-51-6 3'-O-(4,4'-dimethoxytrityl)thymidin-5'-yl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl ethyl phosphonate 
• 3868-27-7 triethylammonium 5'-O-dimethoxytritylthymidine 3'-H-phosphonate 
• 180475-92-7 2,4,6-Trichlorophenyl 5'-O-dimethoxytritylthymidin-3'-yl phosphonate 
• 160056-33-7 Phenyl 5'-O-dimethoxytritylthymidin-3'-yl phosphonate 
• 260262-61-1 4-Nitrophenyl 5'-O-dimethoxytritylthymidin-3'-yl phosphonate 

Relevant academic research and scientific papers

First synthesis of carbocyclic oligothymidylates

5'-O-(dimethoxytrityl)-(+)-carbocyclic thymidine 1 is converted into different 3'-substituted intermediates 2a-c following standard procedures. From these compounds stereochemically pure carbocyclic oligothymidylates 4 are obtained using solid phase synthetic methods.

Expanding the horizon of the thymine Isostere biochemistry: Unique cyclobutane dimers formed by photoreaction between a thymine and a toluene residue in the dinucleotide framework

Substituted toluenyl groups are considered as close isosteres of the thymine residue. They can be recognized by DNA polymerases as if they were thymine. These toluene derivatives are generally inert toward radical additions, including the [2+2] photocycloadditions, due to the stable structure of the aromatic ring and are usually used as solvents for radical reactions. Surprisingly, after incorporating toluene into the dinucleotide framework, we found that the UV excited thymine residue readily dimerizes with the toluenyl moiety through a [2+2] photoaddition reaction. Furthermore, the reaction site on the toluenyl moiety is not the C5=C6 bond, as commonly observed in cyclobutane pyrimidine dimers, but the C4=C5 or C3=C4 instead. Such a reaction pattern suggests that in the stacked structure, it is one of these bonds, not the C5=C6, that is close to the thymine C5=C6 bond. A similar structural feature is found in DNA duplex with a thymine replaced by a 2,4-difluorotoluene. Our results argue that although the substituted toluenyl moieties closely mimic the size and shape of the thymine residue, their more hydrophobic nature determines that they stack on DNA bases differently from the natural thymine residue and likely cause local conformational changes in duplex DNA.

Nucleoside H-phosphonates, XXII: Synthesis and properties of new nucleotide analogues - H-phosphonothiolate diesters

Condensation of nucleoside 3′-H-phosphonate monoesters with various thiols, promoted by condensing agents, provides a convenient access to a new class of H-phosphonate analogues, H-phosphonothiolate diesters. Chemical properties, relevant to possible appl

The case for configurational stability of H-phosphonate diesters in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU)

Configurational stability of dinucleoside H-phosphonates and the stereochemical course of their sulfurisation in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU) were investigated using 31 P NMR spectroscopy. It was found that under the rea

Use of ammonium aryl H-phosphonates in the preparation of nucleoside H-phosphonate building blocks

Ammonium 4-methylphenyl H-phosphonate 4c was used in the conversion of 5'-0-(dimethoxy-trityl)-2'-deoxynucleoside derivatives 6 into the corresponding 3'-H-phosphonates 2, which were isolated in a high state of purity and in high yield.

Use of NPE-protecting groups for the preparation of oligonucleotides without using nucleophiles during the final deprotection

The preparation of O-(4-nitrophenyl)ethyl phosphoramidites and H- phosphonate derivatives of Npe protected nucleosides is described together with the use of these products to prepare oligodeoxynucleotides without using nucleophiles during the final deprot

Nucleoside Phosphite, 0-Bis(1,1,1,3,3,3-hexafluoro-2-propyl) Deoxyribonucleosid-3'-yl Phospites. A Versatile Synthetic Intermediate for Phosphonate Modified Nucleotide and Oligonucleotide Synthesis

The 0-bis(1,1,1,3,3,3-hexa-fluoro-2-propyl) deoxyribonucleosid-3'-yl phosphite units could be converted into the 0-nucleosid-3'-yl phosphonate, 0-2-cyanoethyl 0-nucleosid-3'-yl phosphonate, and 0-1,1,1,3,3,3-hexafluoro-2-propyl 0-nucleosid-3'yl phosphonot

NUCLEOSIDE H-PHOSPHONATES. III. CHEMICAL SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDES BY THE HYDROGENPHOSPHONATE APPROACH

A rapid synthesis of oligodeoxyribonucleotides on solid support is described via coupling of the deoxyribonucleoside 3'-H-phosphonates in the presence of various condensing reagents.

A NEW AND VERSATILE APPROACH TO THE PREPARATION OF VALUABLE DEOXYNUCLEOSIDE 3'-PHOSPHITE INTERMEDIATES

The easily accessible and crystalline monofunctional phosphitylating reagent bis-(diisopropylamino)chlorophosphine has been used for the synthesis of phosphoramidites and H-phosphonates of d-nucleosides and, also, the formation of 3'-5'-internucleotidic phosphonate bonds.