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End date: 2009 × Start date: 2000 × DDC: 540 × Type: article × Subject: Pyrimidines ×

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Now showing 1 - 3 of 3
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    Dimethylaminomethylene-α-D-xylo-hept-5-ulofuranurononitrile as building block in the synthesis of 'reversed' C-nucleoside analogues
    (Berlin : de Gruyter, 2006) Hashmi, I.A.; Feist, H.; Michalik, M.; Reinke, H.; Peseke, K.
    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-S-enofuranuronoyl)benzo[4,5]imidazo[1, 2-a]pyridine-4-carbonitrile (7). © 2006 Verlag der Zeitschrift für Naturforschung.
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    Nucleoside analogues from push-pull functionalized branched-chain pyranosides
    (Berlin : de Gruyter, 2006) Kordian, M.; Feist, H.; Kantlehner, W.; Michalik, M.; Peseke, K.
    The reaction of methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro- hexopyranosid-3-ulose (1) with ethynylmagnesium bromide in tetrahydrofuran and subsequent trimethylsilylation yielded the methyl 4,6-O-benzylidene-2-deoxy-3-C- ethynyl-3-O-trimethylsilyl-α-D-ribo-hexopyranoside (3). Push-pull functionalization of 3 with N,N,N′,N′,N″,N″- hexamethylguanidinium chloride under basic conditions and following deprotection afforded the spiro{2,5-dihydro-3-dimethylamino-furan-2,8'-4',4'a,6',7',8',8'a- hexahydro-6'-methoxy-2'-phenyl-pyrano[3,2-d][1,3]dioxine}-5- ylidenemalononitrile (9). Furthermore, compound 1 reacted with N,N-dimethylformamide dimethylacetal to furnish methyl (E)-4,6-O-benzylidene-2- deoxy-2-dimethylaminomethylene-α-D-erythro-hexopyranosid-3-ulose (10). Treatment of 10 with methylhydrazine and amidines yielded (4S,5aR,8R,9aS)-2,5a, 6,9a-tetrahydro-4-methoxy-2-methyl-8-phenyl-4H-[1,3]dioxino[4',5':5,6]pyrano[4, 3-c]pyrazole (11a) and (2R,4aR,6S,10bS)-4,4a,6,10b-tetrahydro-6-methoxy-2- phenyl[1,3]dioxino[4',5':5,6]pyrano[4,3-d]pyrimidines 12, respectively. © 2006 Verlag der Zeitschrift für Naturforschung.
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    Pyrimidine acyclo-C-nucleosides by ring transformations of 2-formyl-L-arabinal
    (Basel : MDPI, 2005) Bari, A.; Feist, H.; Michalik, M.; Peseke, K.
    The protected 2-formyl-L-arabinal 2 reacted with thiourea and cyanamide in the presence of sodium hydride to afford via ring transformations the 5-[1R,2S-1,2-bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydropyrimidines 3 and 4, respectively. Similarly, treatment of 2 with 3-amino-2H-1,2,4-triazole yielded 6-[1R,25-1,2-bis(benzyloxy)-3-hydroxypropyl][1,2,4]-triazolo[1,5-a]pyrimidine(5) .