Studies on Synthetic Nucleotides. I. A Convenient Synthesis of Ribonucleotides.

Shimizu, Bunji; Asai, Motoji; Nishimura, Tomonori

doi:10.1248/cpb.15.1847

Cited by 11 publications

(3 citation statements)

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“…Hydrolysis of these esters by the action of phosphodiesterase in a buffer solution at pH 9 led to the production of 9-β-D-ribofuranosyl 5'-phosphates of adenine (5'-AMP) and hypoxanthine 175 (IMP). The yields of compounds 172-175 amounted to 38-59, 97, 88, and 39-42% respectively [99][100][101]. …”

Section: Trialkylsilyl Protectionmentioning

confidence: 98%

“…With silyl protection it is possible to produce nucleotides by the condensation of silylpurines with phosphoryl derivatives of sugars. Thus, the fusion of silylpurines 156 with 5-diphenylphosphoryl-2,3-di-O-benzoyl-D-ribofuranosyl bromide at 100-110°C gave 9-substituted silylpurines 171 [99,100]. Treatment of the products with aqueous ethanol and then with NaOH in aqueous dioxane and with sodium methoxide in methanol gave compounds 174.…”

Section: Trialkylsilyl Protectionmentioning

confidence: 99%

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The use of protecting groups in the synthesis of purine derivatives (review)

Александрова

Кочергин²

2009

Chem Heterocycl Comp

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During the synthesis of derivatives of purine from amino-, hydroxy-, thio-, or chloropurines there is often a need at position 2, 6, 7, or 9 of the purine ring to insert a protecting group that can be removed after the necessary chemical operations and retained or replaced by another pharmacophoric group during the search for biologically active substances. ALKYL (ARALKYL) PROTECTION OF POSITION 7(9)The following basic rules were established on the basis of experimental data from a large number of papers and patents relating to the nucleophilic substitution of chloropurines, reported in the monographs [1, 2]: In the series of chloro-, dichloro-, and trichloropurines the most reactive is the chlorine atom at position 6, in second place is the chlorine atom at position 8, and in third place the chlorine atom at position 2 of the purine bicycle. This rule persists in the series of 7(9)-alkyl-2,6-, -2,8-, and -6,8-dichloropurines.In the series of 7(9)-alkyl-2,6,8-trichloropurines the order of nucleophilic substitution of the chlorine atoms changes. In these compounds, unlike 2,6,8-trichloropurine, the most vulnerable center for nucleophilic attack is the chlorine atom at position 8 and then the chlorine atom at position 6 of the purine ring. The chlorine atom at position 2 was and remains the most inert in the series of 7(9)-alkyl-2,6,8-trichloropurines.In the synthesis of 8-substituted purines from 2,6,8-trichloro-7-methylpurine (1) the founder of purine chemistry E. Fischer used the methyl group as protection. Thus, 2,6-dichloro-7-methylpurin-8-one (2) was obtained by the reaction of the trichloride 1 with KOH in aqueous solution at 20°C [3].

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Section: Trialkylsilyl Protectionmentioning

confidence: 98%

Section: Trialkylsilyl Protectionmentioning

confidence: 99%

The use of protecting groups in the synthesis of purine derivatives (review)

Александрова

Кочергин²

2009

Chem Heterocycl Comp

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“…Thus, the acyl derivatives of 2 were generated by the condensation of dithyminylmercury-[ 11, 2,4-di-O-ethyl- [2], or 2,4-di-O-trimethylsilyI- [3] [4] -thymine with 2'. 3', 5'-tri-0-benzoyl-(or acetyl) -D-ribofuranosyl halides.…”

mentioning

confidence: 99%

Synthesis of 5‐Methyluridine and Its 5′‐Mercapto‐, 2‐Amino‐, and 4′,5′‐Unsaturated Analogues

Škarié

Matulié-Adamié

1980

Helvetica Chimica Acta

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The stereospecific cis-hydroxylation of 1-(2,3-dideoxy-P-~-glyceropent-2-enofuranosy1)thymine (1) into 1 -P-D-ribofuranosylthymine (2) by osmium tetroxide is described. Treatment of 2', 3'-0,O-isopropylidene-5-methyl-2,5'-anhydrouridine (8) with hydrogen sulfide or methanolic ammonia afforded 5'-deoxy-2', 3'-0, O-isopropylidene-5'-mercapto-5-methyluridine (9) and 2',3'-0,O-isopropylidene-5-methyl-isocytidine (lo), respectively. The action of ethanolic potassium hydroxide on 5'-deoxy-5'-iodo-2', 3'-0,O-isopropylidene-5-methyluridine (7) gave rise to the corresponding l-(~-deoxy-~-~-erythropent-4-enofuranosyl)5-methyluracil (13) and 2-0-ethyl-5 -methyluridine (14).The hydrogenation of 2 and its 2', 3'-0,O-isopropylidene derivative 4 over 5% Rh/A120, as catalyst generated diastereoisomers of the corresponding 5-methyl-5,6dihydrouridine (17 and 18).

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Preparation and mass spectral characterization of pentafluorobenzyl derivatives of alkyl and hydroxyalkyl-nucleobase DNA adducts

Saha

Kresbach

Giese

et al. 1989

Biol. Mass Spectrom.

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Pentafluorobenzyl (PFBz) derivatives of the following nucleobases were prepared: cytosine, 5-methylcytosine, O2-methylcytosine, O2-ethylthymine, O4-ethylthymine, 5-hydroxymethyluracil, N6-methyladenine, O6-methylguanine, O6-hydroxyethylguanine and O6-hydroxyethylpurine. 13C nuclear magnetic resonance was diagnostic for O- versus N-attachment of the PFBz moiety: the resonance of the methylene carbon appeared in the range 29.15-42.13 ppm for NCH2C6F5, and 58.45-69.01 for OCH2C6F5. Considerable structural information was provided by mass spectrometry with ionization by electron impact. All of the derivatives were detected with high sensitivity and specificity by gas chromatography with detection by electron capture negative ion mass spectrometry, reflecting not only their chemical and physical stability, but also their strong tendency to form a structurally diagnostic anion, [M - PFBz]-, in high yield under these ionization conditions. PFBz derivatives are therefore attractive forms of alkyl-substituted nucleobases for analysis by mass spectrometry.

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Studies on Synthetic Nucleotides. I. A Convenient Synthesis of Ribonucleotides.

Cited by 11 publications

References 0 publications

The use of protecting groups in the synthesis of purine derivatives (review)

The use of protecting groups in the synthesis of purine derivatives (review)

Synthesis of 5‐Methyluridine and Its 5′‐Mercapto‐, 2‐Amino‐, and 4′,5′‐Unsaturated Analogues

Preparation and mass spectral characterization of pentafluorobenzyl derivatives of alkyl and hydroxyalkyl-nucleobase DNA adducts

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