- A convenient synthesis of N4,O3′,O 5′-triacetyl-2′-ketocytidine
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A convenient synthesis of the title compound in four steps from cytidine is reported. Key transformations include differentiation of the 2' position as N4,O3′,O5′ triacetyl-2,2′-anhydrocytidine, opening to the arabino derivative, and oxidation of the 2′ position with the Dess-Martin reagent. Copyright
- Kjell, Douglas P.,Slattery, Brian J.
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- Phosphonate analogues of cytosine arabinoside monophosphate
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Phosphonate derivatives of cytidine and cytosine arabinoside have been prepared from the corresponding nucleoside aldehydes and tested for their ability to serve as substrates for nucleotide monophosphate kinase and for their toxicity to K562 leukemia cells.
- Chen, Xuemei,Jung, Kang-Yeoun,Wiemer, David F.,Wiemer, Andrew J.,Hohl, Raymond J.
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- Synthesis of regioselectively protected forms of cytidine based on enzyme-catalyzed deacetylation as the key step
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N4-Acetylcytidine (77%) and 2′,3′-O, N4-triacetylcytidine (95%) were obtained from the hydrolysis of a common precursor, the peracetylated form of cytidine with Aspergillus niger lipase (Amano A) and Burkholderia cepacia esterase (SC esterase S), respectively, under very mild conditions. The experimental procedure for the conversion of triacetylcytidine to a corresponding phosphoramidite (82%), an intermediate for sugar nucleotide synthesis, is also elaborated.
- Kuboki, Atsuhito,Ishihara, Takashi,Kobayashi, Eiko,Ohta, Hiromichi,Ishii, Takeshi,Inoue, Ayumu,Mitsuda, Satoshi,Miyazaki, Tatsuo,Kajihara, Yasuhiro,Sugai, Takeshi
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- Stereoselective synthesis of the 5′-hydroxy-5′-phosphonate derivatives of cytidine and cytosine arabinoside
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Both the (R)- and (S)-5′-hydroxy 5′-phosphonate derivatives of cytidine and cytosine arabinoside (ara-C) have been prepared via phosphite addition or a Lewis acid mediated hydrophosphonylation of appropriately protected 5′-nucleoside aldehydes. Phosphite addition to a cytosine aldehyde protected as the 2′,3′-acetonide gave predominately the 5′R isomer, while phosphite addition to the corresponding 2′,3′-bis TBS derivative favored the 5′S stereochemistry. In contrast, phosphite addition to the 2′,3′-bis TBS protected aldehyde derived from ara-C gave only the 5′R adduct. However, TiC4-mediated hydrophosphonylation of the same ara-C aldehyde favored the 5′S stereoisomer by a 2:1 ratio. Once all four of the diastereomers were in hand, the stereochemistry of these compounds could be assigned based on their spectral data or that obtained from their O-methyl mandelate derivatives. After hydrolysis of the phosphonate esters and various protecting groups, the four α-hydroxy phosphonic acids were tested for their ability to serve as substrates for the enzyme nucleoside monophosphate kinase and for their toxicity to K562 cells.
- Chen, Xuemei,Wiemer, Andrew J.,Hohl, Raymond J.,Wiemer, David F.
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- Preparation method of 3'-deoxyuridine
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The invention relates to the field of pharmaceutical synthesis and particularly relates to a preparation method of 3'-deoxyuridine. The method comprises the steps: by adopting a compound 3 as a raw material, firstly protecting amino through acetic anhydride to obtain a compound 4, obtaining a compound 5 under the action of acetyl bromide, reducing through a hypophosphite system to obtain a compound 6; removing deacetylated amino under the action of high-pressure water vapor and an organic solvent to obtain a compound 8 or removing N-acetyl to obtain a compound 7; and finally removing all acetyl to obtain a mixture of 3'-deoxyuridine and 3'-deoxycytidine; separating and purifying to obtain 3'-deoxyuridine crystal and 3'-deoxycytidine crystal separately, or directly removing all acetyl through the compound 6 to obtain the 3'-deoxycytidine. Available natural products are taken as initial raw materials, so that the method is simple in operation and convenient to purify, and industrial large-scale production is extremely easy to implement.
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Paragraph 0033; 0034; 0035; 0036
(2017/09/02)
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- SUBSTITUTED NUCLEOSIDE AND NUCLEOTIDE ANALOGS
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Disclosed herein are nucleotide analogs with protected phosphates, methods of synthesizing nucleotide analogs with protected phosphates and methods of treating diseases and/or conditions such as viral infections, cancer, and/or parasitic diseases with the nucleotide analogs with protected phosphates.
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Page/Page column 138
(2010/10/03)
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- Electron-deficient benzotriazoles for the selective N-acetylation of nucleosides
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The use of an acetylated benzotriazole for the selective protection of the amino groups of cytidine and 2′-deoxycytidine is reported. The use of the acetyl group is of considerable interest industrially in this role, and a single-step protection strategy advantageous in bulk production. 1-Acetyl-4-nitrobenzotriazole was found to readily acetylate the amine of cytidine preferentially over the exposed alcohol functionalities. With adaptation of the protocol, 2′-deoxycytidine was protected using the same reagent. A similar approach was attempted for the benzoylation of adenosine but was found to be unsuitable.
- Reid, Andrew K.,McHugh, Callum J.,Richie, Graham,Graham, Duncan
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p. 4201 - 4203
(2007/10/03)
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- Preparation of deoxynucleosides
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Methods for preparing deoxynucleosides from their corresponding ribonucleosides by forming 3-tert-butylphenoxythiocarbonylderivatives of the ribonucleosides and subsequently effecting radical deoxygenation reactions at the carbon atoms to be deoxygenated.
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Page column 13
(2008/06/13)
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- Anti-HCV nucleoside derivatives
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The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.
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- 2'-OMe CAC phosphoramidite and methods for preparation and use thereof
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A compound of the general formula STR1 wherein R is alkyl of 1 to about 10 carbons and R' is selected from the group consisting of trityl and pixyl, for use in the synthesis of 2'-OMe RNA sequences. Fast cleavage and deprotection of oligonucleotides is facilitated by the use of a reagent comprising methylamine as active component in place of the traditional reagent ammonium hydroxide.
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- The synthesis of allyl- and allyloxycarbonyl-protected RNA phosphoramidites. Useful reagents for solid-phase synthesis of RNAs with base-labile modifications
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The synthesis of allyl- and allyloxycarbonyl (AOC)-protected RNA phosphoramidites is reported. The use of allyl and AOC groups allows the chemistry of solid-phase RNA synthesis to be expanded to include base-labile modified nucleosides, such as acetylcytidine. The allyl- and AOC-protective chemistry can be further expanded for the construction of RNAs on solid supports and affinity columns.
- Bogdan, Felicia M.,Chow, Christine S.
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p. 1897 - 1900
(2007/10/03)
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- Microwaves - A powerful tool for the base protection of cytidine
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Use of microwaves for the base protection of cytidine is described. The procedure gives N-acylcytidine in nearly quantitative yield in 40-60 seconds.
- Nahar, Pradip
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p. 7253 - 7254
(2007/10/03)
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- Simple synthesis of 4-thiothymidine, 4-thiouridine and 6-thio-2′-deoxyguanosine
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4-triazolo-pyrimidine nucleosides and 6-O-(mesitylenesulfonyl)-2′-deoxyguanosine, when treated with thiolacetic acid at room temperature, gave the corresponding 4-thiopyrimidine nucleosides and 6-thio-2′-deoxyguanosine with high yields (86-93%). Possible mechanisms are discussed.
- Xu, Yao-Zhong,Zheng, Qinguo,Swann, Peter F.
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p. 2817 - 2820
(2007/10/02)
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- THE USE OF LABILE BASE PROTECTING GROUPS IN OLIGORIBONUCLEOTIDE SYNTHESIS
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The use of phenoxyacetyl group for the protection of the exocyclic amino function of purine bases and acetyl group for cytosine in oligonucleotide synthesis by the cyanoethylphosphoramidite approach is described.A side reaction - i.e. partial replacement of phenoxyacetyl group of protected guanines by acetyl group - was observed during the capping step.It can be avoided by the use of phenoxyacetic anhydride in place of acetic anhydride.
- Chaix, Carole,Molko, Didier,Teoule, Robert
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- NUCLEIC ACID RELATED COMPOUNDS. 42. A GENERAL PROCEDURE FOR THE EFFICIENT DEOXYGENATION OF SECONDARY ALCOHOLS. REGIOSPECIFIC AND STEREOSELECTIVE CONVERSION OF RIBONUCLEOSIDES TO 2 prime -DEOXYNUCLEOSIDES.
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Treatment of unhindered secondary alcohols with phenoxythiocarbonyl chloride (phenyl chlorothionocarbonate) in pyridine/dichloromethane, or in acetonitrile with 4-dimethylaminopyridine catalysis for hindered alcohols, gave clean conversion to their O-phenoxythiocarbonyl derivatives. Reductive deoxygenation of these phenyl thionocarbonate esters proceeded smoothly, using tri-n-butyltin hydride and a free radical initiator in warm toluene. Overall conversion yields ranged from 57 to 78% for the naturally occurring nucleosides, nucleoside antibiotics, and methyl beta -D-ribofuranoside.
- Robins,Wilson,Hansske
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p. 4059 - 4065
(2007/10/02)
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