Synthesis of Novel Anellated Pyranosides as Precursors of C‐Nucleoside Analogues Using Isopropyl 6‐O‐Acetyl‐3‐deoxy‐4‐S‐ethyl‐4‐thio‐α‐D‐threo‐hexopyranosid‐2‐ulose

Autor:	Helmut Reinke, Manfred Michalik, Klaus Peseke, José Agustín Quincoces Suárez, Iran Otero Martinez, Reinaldo Molina Ruiz
Rok vydání:	2004
Předmět:	chemistry.chemical_classification Methylhydrazine Double bond Stereochemistry Organic Chemistry Hydrazine Thio Biochemistry chemistry.chemical_compound Hydroxylamine chemistry Methylene Derivative (chemistry) Isopropyl
Zdroj:	Journal of Carbohydrate Chemistry. 23:337-351
ISSN:	1532-2327 0732-8303
DOI:	10.1081/car-200035744
Popis:	Isopropyl 6‐O‐acetyl‐3‐deoxy‐4‐S‐ethyl‐4‐thio‐α‐D‐threo‐hexopyranosid‐2‐ulose (3) was converted to the corresponding 3‐[bis(methylthio)methylene] derivative 4 with a push–pull activated C–C double bond. Treatment of 4 with hydrazine and methylhydrazine afforded the pyrano[3,4‐c]pyrazol‐5‐ylmethyl acetates 5a and 5b, respectively. Desulfurization of compound 4 with sodium boron hydride yielded the 3‐[(methylthio)methylene]hexopyranosid‐2‐ulose 7. Compound 7 was reacted with amines to furnish 3‐aminomethylene‐hexopyranosid‐2‐uloses 8, 9. Reaction of 7 with hydrazine hydrate, hydrazines, hydroxylamine, and benzamidine afforded the pyrazolo, isoxazalo, and pyrimido anellated pyranosides (10–13). #Dedicated to Professor Dr. Gunther Oehme on the occasion of his 65th birthday.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3cd0262c76ad5bef9a57cabb9999a862 https://doi.org/10.1081/car-200035744 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.