- A novel phosphitylating reagent for in situ generation of deoxyribonucleoside phosphoramidites
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A new phosphitylating reagent, 2-cyanoethoxy(N,N-diisopropylamino)3-nitro-1,2,4-triazolylphosphine (1), has been prepared and effectively used in in situ generation of 5'-DMT-nucleoside phosphoramidites and automated syntheses of oligonucleotides.
- Zhang, Zhaoda,Tang, Jin Yan
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- ON-DEMAND PHOSPHORAMIDITE SYNTHESIS
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The invention relates to a method of synthesis of phosphoramidites by immobilization of a phosphitylation agent on a resin activated to create a charged resin, then putting in contact with the charged resin with a suitable substrate. Phosphoramidites are synthesized in a few minutes from the application of the starting materials. Thus, the process makes it possible to create specific phosphoramidites on demand when they are needed in other applications. The substrates to be applied are mainly nucleosides, thus making it possible to create nucleoside phosphoramidites for the subsequent synthesis of oligonucleotides.
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Page/Page column 36-38; 48
(2022/01/24)
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- Microwave-assisted preparation of nucleoside-phosphoramidites
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Microwave-assisted phosphitylation of sterically hindered nucleosides is demonstrated to be an efficient method for the preparation of corresponding phosphoramidites (otherwise onerous under standard conditions) and is shown to be general in its applicability. the Partner Organisations 2014.
- Meher,Efthymiou,Stoop,Krishnamurthy
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supporting information
p. 7463 - 7465
(2014/07/07)
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- A new and convenient approach for the preparation of β-cyanoethyl protected trinucleotide phosphoramidites
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Herein we report a convenient approach for the preparation of fully protected trinucleotide synthons to be used for the synthesis of gene libraries. The trinucleotide synthons bear β-cyanoethyl groups at the phosphate residues, and thus can be used in standard oligonucleotide synthesis without additional steps for deprotection and work-up.
- Janczyk, Matthaeus,Appel, Bettina,Springstubbe, Danilo,Fritz, Hans-Joachim,Mueller, Sabine
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p. 1510 - 1513
(2012/03/22)
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- Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry
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Ionic liquids have been used in combination with ball milling on a range of chlorophosphoramidite reagents to phosphitylate nucleosides and 2-deoxynucleosides. The enhanced stability offered by the ionic liquid mediated processes combined with efficient mass transfer induced by ball milling has enabled excellent yields to be obtained even when using small dialkyl amino groups as well as the more commonly used diisopropylamino protection.
- Hardacre, Christopher,Huang, Haifeng,James, Stuart L.,Migaud, Marie E.,Norman, Sarah E.,Pitner, William R.
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p. 5846 - 5848
(2011/06/26)
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- Convenient synthesis of N-unprotected deoxynucleoside 3′- phosphoramidite building blocks by selective deacylation of N-acylated species and their facile conversion to other N-functionalized derivatives
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(Chemical Equation Presented) A new route to N-unprotected deoxynucleoside 3′-phosphoramidite building blocks by use of highly selective N-deacylation of commercially available N-acylated deoxynucleoside 3′-phosphoramidites is described. These compounds could be readily converted to other types of N-protected species by facile N-acylations with acylating reagents.
- Ohkubo, Akihiro,Sakamoto, Kazushi,Miyata, Ken-Ichi,Taguchi, Haruhiko,Seio, Kohji,Sekine, Mitsuo
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p. 5389 - 5392
(2007/10/03)
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- PROCESS FOR PRODUCING PHOSPHOROAMIDITE
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The present invention provides high purity phosphoroamidite products by reducing the amount of impurities of triphosphite which has been additionally produced according to the conventional technique.Phosphoroamidites can be obtained with high purity such that the excess reaction is suppressed by using a reaction activator hardly generating triphosphite.According to the present invention, phosphoroamides can be obtained with high purity, which has heretofore been difficult to suppress the generation of impurities of triphosphite.
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Page/Page column 10
(2008/06/13)
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- Methods of producing phosphitylated compounds
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Provided are methods of producing phosphitylated compounds, including 3′-O-phosphoramidites, comprising the step of reacting a hydroxyl-containing compound with a phosphitylating agent in the presence of a phosphitylation activator selected from the group consisting of: (1) acid-base complexes derived from an amine base of Formula I 1wherein R, R1, and R2 are independently C1-C10 alkyl, C1-C10 cycloalkyl, C1-C10 aryl, C1-C10 aralkyl, C1-C10 heteroalkyl, or C1-C10 heteroaryl; (2) acid-base complexes derived from an amine base of Formula II 2wherein R3, R4, R5, R6, and R7 are independently hydrogen, C1-C10 alkyl, C1-C10 cycloalkyl, C1-C10 aryl, C1-C10 aralkyl, C1-C10 heteroalkyl, or C1-C10 heteroaryl, and at least one of R3, R4, R5 R6, and R7 is not hydrogen.; (3) acid-base complexes derived from a diazabicyclo amine base; (4) zwitterionic amine complexes; and (5) combinations of two or more thereof, to produce a phosphitylated compound.
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- Method of preparing phosphoramidites
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Improved methods for preparation of phosphoramidite compounds are disclosed. The phosphoramidites are useful, for example, for the preparation of oligonucleotides by solid state oligonucleotide synthetic regimes.
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- An improved synthesis of the dinucleotides pdCpA and pdCpdA
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An improved route was developed for the preparation of the dinucleotide hybrid 5′-O-phosphoryl-2′-deoxycytidylyl-(3′ → 5′)adenosine (pdCpA) 7. This simple and concise synthesis involves the successive coupling of 2-cyanoethyl N, N, N′, N′-tetra- isopropylphosphorodiamidite with 4-N-benzoyl-5′-O-(4,4′-dimethoxytrityl)-2′-deoxy-cytidine 1 and 6-N,6-N,2′-O,3′-O-tetrabenzoyladenosine 2 as the key step. Some dinucleotide derivatives bearing different protecting groups were also synthesized and the selective deprotection conditions were studied in detail. The utility and efficiency of this approach has been further demonstrated by its application to the synthesis of total DNA dinucleotide pdCpdA 17 and total RNA dinucleotide 21.
- Zhu, Xue-Feng,Scott, A. Ian
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p. 197 - 211
(2007/10/03)
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- Some Steric Aspects of Synthesis of Oligoribonucleotides by Phosphoramidite Approach on Solid Support
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The influence of 2'-O-substituents (i.e. methyl, tetrahydropyranyl, tert-butyldimethylsilyl) on the chemical synthesis of oligoribonucleotides by phosphoramidite approach on solid support is described and compared with respective 2'-deoxynucleoside derivative.The observations on reactivity of these different 2'-O-protected derivatives at phosphatilation and condensation steps show their strong hindrance dependence.Some other aspects like reactivity of tetrahydropyranyl diastereoisomers, 3'- and 2'-O-phosphoramidites and some chemical properties of 2'-O-(tert-butyldimethylsilyl) protecting group are also presented.
- Kierzek, Ryszard,Rozek, Marek,Markiewicz, Wojciech T.
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p. 507 - 516
(2007/10/02)
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