Convenient Preparation of 2-Deoxy-3,5-di-O-<i>p</i>-toluoyl-α-D-<i>erythro</i>-pentofuranosyl Chloride

Rolland, Valérie; Kotera, Mitsuharu; Lhomme, Jean

doi:10.1080/00397919708007071

Cited by 84 publications

(61 citation statements)

References 22 publications

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“…The sodium salt of 7-nitroindole (6) was generated by treatment of 6 with sodium hydride in acetonitrile and treated with a slight excess of bis(p-toluoyl)-achlorodeoxyribose (7) to afford the b-nucleoside 1 a in 50 % yield. [21,22] No trace of the aanomer was detected in the reaction medium. The b-stereochemistry of the glycosyl bond was ascertained by 1 H NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

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The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

et al. 2000

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On the basis of molecular modeling studies, the 7-nitroindole nucleoside 1 was selected as a suitable photochemical precursor for photochemical generation of the C1' deoxyribosyl radical under irradiation, which led to 2'-deoxyribonolactone. The nitro-indole nucleoside derivatives 1a and 1b were prepared and their conformation was determined by X-ray crystallography and NMR spectroscopy. The photoreaction of these nucleosides gave the corresponding deoxyribonolactone derivatives efficiently, with release of 7-nitrosoindole. This reaction was successfully applied to synthesis of oligonucleotides containing the deoxyribonolactone lesion.

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Section: Resultsmentioning

confidence: 99%

“…The a-chloro sugar 7 was prepared as described. [22] 7-Nitroindole (6) is commercially available from Lancaster. Alternatively we prepared 6 from o-nitroaniline or from ethyl 7-nitroindole 2-carboxylate (ACROS) by described procedures.…”

Section: Methodsmentioning

confidence: 99%

The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

et al. 2000

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“…2-Deoxy-3,5-di-O-p-toluoyl-α-d-erythro-pentafuranosyl chloride, 4-(2′-pyridyl)imidazole and imidazole nucleoside were synthesized according to literature procedures [31][32][33]. DNA synthesis and purification were performed in the DMToff mode on a K&A Laborgeräte H8 DNA/RNA synthesizer as reported previously [15].…”

Section: Methodsmentioning

confidence: 99%

4-(2′-Pyridyl)imidazole as an artificial nucleobase in highly stabilizing Ag(I)-mediated base pairs

2015

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A new artificial nucleoside 2 comprising 4-(2'-pyridyl)imidazole as the nucleobase was devised and incorporated into a series of DNA oligonucleotide duplexes. The propensity of 2 to form metal-mediated homo and hetero base pairs was investigated in various 13mer and 26mer duplexes. The artificial nucleoside readily forms Ag(I)-mediated homo base pairs of the type 2-Ag(I)-2, in which the Ag(I) ion resides in a [2 + 2] coordination environment. In addition, the combination with the previously established imidazole nucleoside 1 leads to the formation of Ag(I)-mediated hetero base pairs (2-Ag(I)-1 and 1-Ag(I)-2) with a [2 + 1] coordination environment. With an increase in the melting temperature of ΔT m = 21.8 °C upon the formation of a Ag(I)-mediated base pair, the 2-Ag(I)-1 pair with the 13mer duplex is the most stabilizing Ag(I)-mediated base pair so far. Generally, the impact of the formation of a metal-mediated base pair on the properties of the DNA duplex was found to be significantly more prominent for shorter, intrinsically less stable duplexes.

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“…Treatment of 8-aza-7-deaza-6-methoxypurine [1,18] with N-chlorosuccinimide (NCS) in DMF gave 4, while the reaction of 8-aza-2-methylthio-7-deaza-6-chloropurine [19] with 1M NaOiPr yielded 8. Glycosylation of compound 4 under nucleobase anion conditions (KOH/ TDA-1) with 2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl chloride (5) [20,21] afforded compound 6 as major product. Likewise, the glycosylation of 8 with 5 gave the regioisomeric N 9 -and N 8 -glycosylated compounds 9 and 10 in nearly 2:1 proportion.…”

Section: Synthesis and Properties Of Monomersmentioning

confidence: 99%

“…After stirring at r.t. for 10 min, 2-deoxy-3, 5-di-O-p-toluoyl-α-D-erythropentofuranosyl chloride (5) [20,21] (1.00 g, 2.57 mmol) were added, and stirring was continued for another 30 min. [4] Insoluble material was filtered off, the solvent evaporated, and the residue subjected to FC (column 40 × 2.5 cm).…”

Section: -Chloro-1-[2-deoxy-35-di-o -(P-toluoyl)-β-d-erythro -Pentomentioning

confidence: 99%

Oligonucleotides Containing Pyrazolo[3,4-d]Pyrimidines: 8-Aza-7-deazaadenines With Bulky Substituents in the 2- or 7-Position

Seela

Jawalekar

Sun

et al. 2005

Nucleosides, Nucleotides & Nucleic Acids

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The synthesis of the 2'-deoxyadenosine analogues 1b, 2b, and 3c modified at the 7- and/or 2-position is described. The effect of 7-chloro and 2-methylthio groups on the duplex stability is evaluated. For that, the nucleosides 1b, 2b, and 3c were converted to the corresponding phosphoramidites 15, 19, and 22, which were employed in the solid-phase oligonucleotide synthesis. In oligonucleotide duplexes, compound 1b forms stable base pairs with dT, of which the separated 1b-dT base pairs contribute stronger than that of the consecutive base pairs. Compound 2b shows universal base pairing properties while its N8 isomer 3c forms duplexes with lower stability.

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Convenient Preparation of 2-Deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl Chloride

Cited by 84 publications

References 22 publications

The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

4-(2′-Pyridyl)imidazole as an artificial nucleobase in highly stabilizing Ag(I)-mediated base pairs

Oligonucleotides Containing Pyrazolo[3,4-d]Pyrimidines: 8-Aza-7-deazaadenines With Bulky Substituents in the 2- or 7-Position

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