Purine Nucleoside Analogues. 11. An Alternative Synthesis of N- and O-Alkyl Derivatives of 9- and 7-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine

Madre, Marina; Panchenko, Natella; Golbraikh, Alexander; Zhuk, Regina; Pandit, Upendra K.; Geenevasen, Jan; Koomen, Gerrit-Jan

doi:10.1135/cccc19990685

CCCC > Archive > 1999, Volume 64 > Issue 4 > p. 685

Purine Nucleoside Analogues. 11. An Alternative Synthesis of N- and O-Alkyl Derivatives of 9- and 7-[(2-Acetoxyethoxy)methyl]-N²-acetylguanine

Marina Madre^a,*, Natella Panchenko^a, Alexander Golbraikh^a, Regina Zhuk^a, Upendra K. Pandit^b, Jan Geenevasen^b and Gerrit-Jan Koomen^b

^a Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia
^b Laboratory of Organic Chemistry, University of Amsterdam, 1018 WS Amsterdam, The Netherlands

Abstract

Alkylations of 9- and 7-[(2-acetoxyethoxy)methyl]-N²-acetylguanine with alkyl halogenides in the presence of base have been investigated affording a new route to the preparation of 1,N²-dimethyl- as well as O⁶-benzyl-9(7)-alkoxyalkylguanines. ¹H NMR spectra revealed that the 1,N²-dimethyl derivatives exist as mixtures of two conformers at room temperature due to the restricted rotation about the C2-N2 bond. These findings agreed with conformational calculations.

Keywords: Purines; Nucleosides; Acyclic nucleoside analogues; Acyclovir; Alkylation.

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