Preparation of 2-pyrimidinone nucleosides from uracil nucleosides

Cech, Dieter; Holý, Antonı́n

doi:10.1135/cccc19772246

Cited by 28 publications

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“…The hydrazino derivative 2 (Scheme 1) can be oxidized in the presence of silver (I) oxide to form the protected 2-aminopurine compound 3 (Scheme 1). This latter reaction is similar to that reported for arabinosyl adenosine (40) and various pyrimidine derivatives (41). Deprotection of the carbohydrate residue and subsequent preparation of the dimethoxytrityl phosphoramidite derivative 6 (Scheme 1), produced a compound suitable for incorporation 5637 I H2NNH2 into oligodeoxynucleotides using phosphite triester synthesis procedures (32).…”

Section: Resuitssupporting

confidence: 53%

“…Oxidation of nucleoside hydrazino derivatives provides a simple procedure for the conversion of R-NHNH2 to R-H as demonstrated originally in the conversion of 8-hydrazino-ara A to ara A (40) and in the synthesis of a variety of pyrimidine derivatives (41). A similar procedure can be easily adapted for the preparation of 2-aminopurine derivatives as described in this report.…”

Section: Discussionmentioning

confidence: 98%

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A new approach to the synthesis of a protected 2-aminopurine derivative and its incorporation into oligodeoxynucleotides containing the Eco RI and Bam HI recognition sites

et al. 1988

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A protected 2-aminopurine nucleoside suitable for incorporation into oligodeoxynucleotides using phosphite triester chemical synthesis procedures has been prepared via oxidation of a purine hydrazino derivative with silver (I) oxide. Five oligodeoxynucleotides containing Eco RI and Bam HI recognition sites have been prepared such that, in the double stranded form, the 2-aminopurine base has either a complementary thymine or cytosine nucleobase. The helix character and thermodynamic parameters for helix formation have been examined.

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Section: Resuitssupporting

confidence: 53%

Section: Discussionmentioning

confidence: 98%

A new approach to the synthesis of a protected 2-aminopurine derivative and its incorporation into oligodeoxynucleotides containing the Eco RI and Bam HI recognition sites

et al. 1988

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“…[11] The approach has been modified subsequently, and m 5 K was successfully prepared by oxidation of 4-hydrazinopyrimidinone nucleosides and rearrangement of the intervening diazene with Ag 2 O in refluxing aqueous dioxane or EtOH. [12] Holy published a method using 4-thiopyrimidines and deactivated Raney-Ni. [13] Both methods led to m 5 K in about 40-50 % yield, although the yields were found to be better with ribonucleosides.…”

Section: Introductionmentioning

confidence: 99%

“…Analytical data were identical with those published previously. [12,13] Starting with di-TBDMS-protected m 5 K 5 (500 mg, 1.1 mmol), m 5 K 1 (247 mg, 1.1 mmol, 100 %) was isolated. The pH-driven diffusion experiment was carried out with the same experimental setup, except that no PLE was added to the acceptor phase A.…”

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confidence: 99%

Synthesis and Properties of Fluorescent cycloSal Nucleotides Based on the Pyrimidine Nucleoside m⁵K and Its 2′,3′‐Dideoxy Analog dm⁵K

Jessen¹,

Fendrich²,

Meier³

2006

Eur J Org Chem

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The synthesis of the fluorescent thymidine nucleoside analog 5-methyl-pyrimidin-2-one nucleoside 1 (m 5 K) and that of its 2Ј,3Ј-dideoxy derivative 2 (dm 5 K) are described. Moreover, the conversion of 1 and 2 into the corresponding 3-methylcycloSal-phosphate triesters 11 and 12 or an enzyme-cleavable prodrug 5-acetoxymethylpropionate-cycloSal-phosphate triester 13, and the fluorescence and hydrolysis proper-

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“…The 4-thio derivative 11 was debenzoylated with methanolic ammonia to give free 5-benzyl-4-thiouridine (12). It was also converted into the protected 4-methylthio derivative 13 by reaction with methyl iodide in dimethylformamide.…”

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confidence: 99%

Preparation of 5-Benzyluracil and 5-Benzylcytosine Nucleosides as Potential Inhibitors of Uridine Phosphorylase

Krečmerová

Hřebabecký

Holý

1996

Collect. Czech. Chem. Commun.

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Reaction of 3,4,6-tri-O-acetyl-2-deoxyglucopyranosyl bromide (1) with silylated 5-benzyluracil and subsequent ammonolysis afforded α- and β-anomers of 5-benzyl-1-(2-deoxy-D-glucopyranosyl)uracil (2 and 3). Under catalysis with tin tetrachloride, silylated 5-benzyluracil reacted with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose to give 2',3',5'-tri-O-benzoyl-5-benzyluridine (10), which was converted into the 4-thio derivative 11 by reaction with Lawesson reagent. Debenzoylation of compound 11 afforded 5-benzyl-4-thiouridine (12), whereas its reaction with methyl iodide and deblocking gave 4-methylthiopyrimidine nucleoside 14. Amonolysis of derivative 12 at elevated temperature afforded 5-benzylcytidine (15). This reacted with thionyl chloride at room temperature to give cyclic sulfite 16 which on heating at 100 °C in dimethylformamide was converted into 5-benzyl-2,2'-cyclocytidine (17). Mild alkaline hydrolysis of compound 17 afforded 1-(β-D-arabinofuranosyl)-5-benzylcytosine (18). With boiling thionyl chloride, compound 15 formed 2',3'-cyclic sulfite 19 which on alkaline hydrolysis gave 5-benzyl-5'-chloro-5'-deoxycytidine (20). Compound 20 was reduced with tributylstannane to 5-benzyl-5'-deoxycytidine (21). Reaction of silylated 5-benzyluracil with 2-deoxy-3,5-bis(O-p-toluoyl)-D-ribofuranosyl chloride, catalyzed with mercury(II) bromide, afforded 5-benzyl-2'-deoxy-3',5'-bis(O-p-toluoyl)uridine (22) and its α-anomer 23. With Lawesson reagent, compound 22 gave 5-benzyl-4-thiouracil derivative 24 which was ammonolyzed to give 5-benzyl-2'-deoxycytidine (25). Analogously, compound 23 was converted into 5-benzyl-2-deoxy-α-cytidine (27). 5'-O-Benzoyl-5-benzyluridine (29) was converted into the 2,2'-anhydro derivative 30 which on reaction with hydrogen chloride afforded 3'-chloro-3'-deoxynucleoside 31. This compound was reduced with tributylstannane and the obtained 2'-deoxynucleoside 32 on treatment with thionyl chloride gave a mixture of erythro- and threo-3'-chloro-2',3'-dideoxynucleosides (33 and 34, respectively) which were reduced to 5'-O-benzoyl-5-benzyl-2',3'-dideoxyuridine (35). Compound 35 reacted with Lawesson reagent under formation of 4-thiouracil derivative 36 and this was deblocked to 5-benzyl-4-thio-2',3'-dideoxyuridine (37). On heating with ammonia, compound 37 was converted into 5-benzyl-2',3'-dideoxycytidine (38). Reaction of 4-thiouracil derivative with methyl iodide and subsequent hydrazinolysis afforded 4-hydrazino derivative 40 which was heated with silver oxide in ethanol to give a mixture of anomeric 5-benzyl-1-(2,3-dideoxyribofuranosyl)-2(1H)-pyrimidinones (42).

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Preparation of 2-pyrimidinone nucleosides from uracil nucleosides

Cited by 28 publications

References 0 publications

A new approach to the synthesis of a protected 2-aminopurine derivative and its incorporation into oligodeoxynucleotides containing the Eco RI and Bam HI recognition sites

A new approach to the synthesis of a protected 2-aminopurine derivative and its incorporation into oligodeoxynucleotides containing the Eco RI and Bam HI recognition sites

Synthesis and Properties of Fluorescent cycloSal Nucleotides Based on the Pyrimidine Nucleoside m⁵K and Its 2′,3′‐Dideoxy Analog dm⁵K

Preparation of 5-Benzyluracil and 5-Benzylcytosine Nucleosides as Potential Inhibitors of Uridine Phosphorylase

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Preparation of 2-pyrimidinone nucleosides from uracil nucleosides

Cited by 28 publications

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A new approach to the synthesis of a protected 2-aminopurine derivative and its incorporation into oligodeoxynucleotides containing the Eco RI and Bam HI recognition sites

A new approach to the synthesis of a protected 2-aminopurine derivative and its incorporation into oligodeoxynucleotides containing the Eco RI and Bam HI recognition sites

Synthesis and Properties of Fluorescent cycloSal Nucleotides Based on the Pyrimidine Nucleoside m5K and Its 2′,3′‐Dideoxy Analog dm5K

Preparation of 5-Benzyluracil and 5-Benzylcytosine Nucleosides as Potential Inhibitors of Uridine Phosphorylase

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Synthesis and Properties of Fluorescent cycloSal Nucleotides Based on the Pyrimidine Nucleoside m⁵K and Its 2′,3′‐Dideoxy Analog dm⁵K