Synthesis of 2-Methoxyinosine and Its 5'-Phosphate

Yamazaki, Akihiro; Saito, Tatsuhiro; Yamada, Yoshitaka; Kumashiro, Izumi

doi:10.1248/cpb.17.2581

Cited by 5 publications

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“…It was shown that the pyrazole dioxime 89 gives the pyrazolo [3,4-c]furazan derivative 90 with a yield of 70% when heated in acetic anhydride in the presence of sodium acetate [133,134]. Several papers have been devoted to the synthesis of the imidazolopyrimidine [135,136] and pyrazolopyrimidine [137] systems from the corresponding derivatives of imidazole and pyrazole oximes. For example, the reaction of the oximes 91 with ethyl orthoformate leads to pyrazolo [3,4-d]pyrimidines 92 [137].…”

mentioning

confidence: 99%

Oximes of five-membered heterocyclic compounds with two heteroatoms 2. Reactions and biological activity (Review)

Абеле

Lukevics

2007

Chem Heterocycl Comp

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mentioning

confidence: 99%

Oximes of five-membered heterocyclic compounds with two heteroatoms 2. Reactions and biological activity (Review)

Абеле

Lukevics

2007

Chem Heterocycl Comp

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ChemInform Abstract: SYNTH. VON 2‐METHOXYINOSIN UND SEINES 5′‐PHOSPHATS

Yamazaki¹,

Saito²,

Yamada³

et al. 1970

Chemischer Informationsdienst. Organische Chemie

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7‐(β‐D‐Arabinofuranosyl)‐2, 4‐dichlor‐7H‐pyrrolo[2,3‐d]pyrimidin – Synthese, selektiver Halogenaustausch und Einfluß glyconischer Schutzgruppen auf die Reaktivität des Aglycons

Seela

Driler

1984

Liebigs Ann. Chem.

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2,4-Dichlor-7H-pyrrolo[2,3-d]pyrimidin (la) wurde mit der Arabinohalogenose 5 selektiv an N-7 glycosyliert und das p-Anomer 7a in 67 070 Ausbeute erhalten. Debenzylierung rnit Bortrichlorid ergibt das 2,4-Dichlornucleosid 2, bei dem die Zuordnung der Glycosylierungsposition durch 13C-NMR-Fernkopplung mit dem Anomerenproton erfolgte. Nucleophile Substitution fiihrt bei 2 selektiv zum Ersatz des C-4-, unter forcierten Bedingungen des C-2-und C-CSubstituenten, womit sich 2 als gemeinsame Vorstufe fur die Synthese von aru-7-Desazapurin-Nucleosiden anbietet. Im Gegensatz zum freien Nucleosid 2 ist die nucleophile Substitution an der benzylgeschiitzten Vorstufe 7a stark erschwert. trichloride results in the formation of the 2,4-dichloronucleoside 2. The assignment of the position of glycosylation was made on the basis of 13C NMR long-range coupling with the anomeric proton. Nucleophilic displacement on compound 2 results in selective substitution of the halogen in position 4. By applying more vigorous conditions the C-4 as well as the C-2 substituents are replaced. Therefore, 2 represents a common intermediate for the synthesis of uru-7-deazapurine nucleosides. In contrast to 2, nucleophilic substitution at the benzyl-protected precursor 7a is hindered.

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Synthesis of 2-Methoxyinosine and Its 5'-Phosphate

Cited by 5 publications

References 0 publications

Oximes of five-membered heterocyclic compounds with two heteroatoms 2. Reactions and biological activity (Review)

Oximes of five-membered heterocyclic compounds with two heteroatoms 2. Reactions and biological activity (Review)

ChemInform Abstract: SYNTH. VON 2‐METHOXYINOSIN UND SEINES 5′‐PHOSPHATS

7‐(β‐D‐Arabinofuranosyl)‐2, 4‐dichlor‐7H‐pyrrolo[2,3‐d]pyrimidin – Synthese, selektiver Halogenaustausch und Einfluß glyconischer Schutzgruppen auf die Reaktivität des Aglycons

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