Dimethylaminomethylene-α-D-xylo-hept-5-ulofuranurononitrile as Building Block in the Synthesis of ‘Reversed’ C-Nucleoside Analogues

Autor:	Manfred Michalik, Klaus Peseke, Holger Feist, Helmut Reinke, Imran Ali Hashmi
Rok vydání:	2006
Předmět:	Guanidinium chloride chemistry.chemical_compound chemistry Stereochemistry Sodium Block (telecommunications) chemistry.chemical_element General Chemistry C nucleosides Sulfate
Zdroj:	Zeitschrift für Naturforschung B. 61:292-300
ISSN:	1865-7117 0932-0776
DOI:	10.1515/znb-2006-0309
Popis:	3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-6-(dimethylaminomethylene)-α-D-xylo-hept-5-ulofuranurononitrile (1) was reacted with amidinium salts, S-methylisothiouronium sulfate, and guanidinium chloride, respectively, in the presence of bases to furnish the 4-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-4-yl)pyrimidine-5-carbonitriles 2 and the 4-(1,2-O-isopropylidene- α-D-glycero-tetr-3-enofuranos-4-yl)pyrimidine-5-carbonitriles 3, respectively. Treatment of 1 with ethyl 5-aminopyrazole-4-carboxylates yielded the ethyl 7-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-4-yl)-6-cyanopyrazolo[1,5-a]pyrimidine-3-carboxylates 4 and the ethyl 7-amino-6-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentofuranuronoyl)pyrazolo[1,5-a]pyrimidine- 3-carboxylates 5, respectively. Reaction of 1 with 2-benzimidazolylacetonitrile in the presence of sodium methanolate afforded 1-amino-2-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentofuranuronoyl) benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (6) and 1-amino-2-(3-deoxy-1,2-O-isopropylidene- α-D-glycero-pent-3-enofuranuronoyl)benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile (7).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a924bfa6fe4c9acd7500f18d1c78fbb9 https://doi.org/10.1515/znb-2006-0309 Zobrazit plný text záznamu