The Synthesis of Nucleoside 5'-O-(1,1-Dithiotriphosphates)

Okruszek, And̀rzej; Olesiak, Magdalena; Balzarini, Jan

doi:10.1021/jm00048a021

Cited by 28 publications

(21 citation statements)

References 10 publications

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“…16,17 On the other hand, because chromatographic separation of nucleoside-5 0 -O-oxathiaphospholane monomers, carrying typical protecting groups at the 3 0 -or 2 0 -and 3 0 -hydroxyl functions, could not be achieved, numerous P-chiral biophosphates were synthesized using unresolved monomers (e.g., 8, Scheme 3). [18][19][20] Here, we report on the synthesis of selected 3 0 -O-acylated deoxyribonucleoside-and 2 0 ,…”

Section: Nucleosidementioning

confidence: 99%

Diastereomerically pure nucleoside‐5′‐O‐(2‐thio‐4,4‐pentamethylene‐1,3,2‐oxathiaphospholane)s—Substrates for synthesis of P‐chiral derivatives of nucleoside‐5′‐O‐phosphorothioates

2010

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A method for stereocontrolled chemical synthesis of P-substituted nucleoside 5'-O-phosphorothioates has been elaborated. Selected 3'-O-acylated deoxyribonucleoside- and 2',3'-O,O-diacylated ribonucleoside-5'-O-(2-thio-4,4-pentamethylene-1,3,2-oxathiaphospholane)s were chromatographically separated into P-diastereomers. Their reaction with anions of phosphorus-containing acids was highly stereoselective (≥90%) and furnished corresponding P-chiral α-thiodiphosphates and their phosphonate analogs with satisfactory yield.

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Section: Nucleosidementioning

confidence: 99%

Diastereomerically pure nucleoside‐5′‐O‐(2‐thio‐4,4‐pentamethylene‐1,3,2‐oxathiaphospholane)s—Substrates for synthesis of P‐chiral derivatives of nucleoside‐5′‐O‐phosphorothioates

2010

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“…Carbohydrate phosphates have been the subject of study of nucleosides and their prodrugs with improved cellular permeability and antiviral or anticancer activities . Monothiophosphorylated and dithiophosphorylated carbohydrates were also obtained . Meanwhile, due to their chirality at the phosphorus center and higher stability toward enzymatic hydrolysis, phosphorothioate derivatives have proven to be valuable as model constructs for designing enzyme‐catalyzed phosphoryl transfer reactions .…”

Section: Introductionmentioning

confidence: 99%

α‐d‐Glucofuranose and α‐d‐allofuranose diacetonides and silyl ether of α‐d‐glucofuranose diacetonide in dithiophosphorylation reactions

Низамов

Nikitin

Belov

et al. 2016

Heteroatom Chemistry

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α‐d‐Glucofuranose and α‐d‐allofuranose diacetonides react with 2,4‐diorganyl 1,3,2,4‐dithiadiphosphetane‐2,4‐disulfides to form optically active dithiophosphonates in 78–81% yields, which are transformed into the corresponding ammonium salts in 90–97% yields by the treatment of n‐hexadecylamine. The S‐silyldithiophosphonate was prepared in 93% yield by the reaction of 2,4‐bis(butoxyphenyl) 1,3,2,4‐dithiadiphosphetane‐2,4‐disulfide with silyl ether of α‐d‐glucofuranose diacetonide. One of the salts obtained possesses antibacterial activity against Staphylococcus aureus ATCC 6538‐P.

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“…6,7 A number of approaches have focused on modifications and/or substitutions on the base, 8,9 carbohydrate 10–15 and linear triphosphate moieties 16–21 to design modified nucleotides for diverse applications in nucleic acid and antiviral research.…”

mentioning

confidence: 99%

Synthesis of β-triphosphotriester pronucleotides

Beni

Dash

Parang

2015

Tetrahedron Letters

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Dinucleoside phosphorochloridite were synthesized from phosphorus trichloride and three nucleoside analogues, 3′-fluoro-2′,3′-dideoxythymidine (FLT), 2′,3′-dideoxy-5-fluoro-3′-thiacytidine (FTC), and 2′,3′-dideoxy-3′-thiacytidine (3TC), in a multistep synthesis. Polymer-bound N-Boc p-acetoxybenzyl 5′-O-2′-deoxythymidine was reacted with dinucleoside phosphorochloridite in the presence of 2,6-lutidine, followed by the reaction with dodecyl alcohol and 5-(ethylthio)-1H-tetrazole, oxidation with tert-butyl hydroperoxide, and acidic cleavage, respectively, to afford the β-triphosphotriester derivatives containing three different nucleosides.

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The Synthesis of Nucleoside 5'-O-(1,1-Dithiotriphosphates)

Cited by 28 publications

References 10 publications

Diastereomerically pure nucleoside‐5′‐O‐(2‐thio‐4,4‐pentamethylene‐1,3,2‐oxathiaphospholane)s—Substrates for synthesis of P‐chiral derivatives of nucleoside‐5′‐O‐phosphorothioates

Diastereomerically pure nucleoside‐5′‐O‐(2‐thio‐4,4‐pentamethylene‐1,3,2‐oxathiaphospholane)s—Substrates for synthesis of P‐chiral derivatives of nucleoside‐5′‐O‐phosphorothioates

α‐d‐Glucofuranose and α‐d‐allofuranose diacetonides and silyl ether of α‐d‐glucofuranose diacetonide in dithiophosphorylation reactions

Synthesis of β-triphosphotriester pronucleotides

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