Nucleoside Analogues from Branched-Chain Pyranosides
Iran Otero A B , Holger Feist A , Lidcay Herrera A , Manfred Michalik C , José Quincoces D and Klaus Peseke A EA Universität Rostock, Fachbereich Chemie, 18051 Rostock, Germany.
B Facultad de Química y Farmacia, Universidad Central de Las Villas, Cuba.
C Leibniz-Institut für Organische Katalyse, 18055 Rostock, Germany.
D Universidade Bandeirante de São Paolo, São Paolo, CEP: 02071-013, Brazil.
E Corresponding author. Email: klaus.peseke@chemie.uni-rostock.de
Australian Journal of Chemistry 58(2) 104-111 https://doi.org/10.1071/CH04168
Submitted: 7 July 2004 Accepted: 9 December 2004 Published: 21 February 2005
Abstract
Reaction of (pyranosid-3-yl)ethanal 2 with ethynylmagnesium bromide or lithium phenylacetylide in THF afforded (2R,S)-1-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-yl)but-3-yn-2-ols 3a and 3b, respectively. Oxidation of 3a and 3b yielded the 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-yl)but-3-yn-2-ones 4a and 4b, which upon treatment with hydrazine and hydrazine derivatives formed the 3-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-ylmethyl)pyrazoles 5a–5d. Compounds 4a and 4b also underwent reaction with amidinium and guanidinium salts under basic conditions to furnish the 4-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-ylmethyl)pyrimidines 8a–8f. Furthermore, treatment of 4a and 4b with 2-aminobenzimidazole yielded the 2-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-ylmethyl)benzo[4,5]imidazo[1,2-a]pyrimidines 11a and 11b. Deprotection of 5a and 8b in two steps afforded 3(5)-(methyl 3-deoxy-α-d-altropyranosid-3-ylmethyl)-1H(2H)-pyrazole 7 and 4-(methyl 3-deoxy-α-d-altropyranosid-3-ylmethyl)-2-phenylpyrimidine 10, respectively. Compound 11a was treated with AcOH/H2O to furnish 2-(methyl 2-O-benzyl-3-deoxy-α-d-altropyranosid-3-ylmethyl)benzo-[4,5]imidazo[1,2-a]pyrimidine 13.
Acknowledgments
The authors thank the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie for financial support. J.Q. is grateful to the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP, Brasil). I.O. is grateful to the Deutscher Akademischer Austauschdienst for a scholarship.
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