Purine nucleoside analogues. 11. An alternative synthesis of N- and O-alkyl derivatives of 9-and 7-[(2-acetoxyethoxy)methyl]-N-2-acetylguanine

Authors
Madre, M Panchenko, N Golbraikh, A Zhuk, R Pandit, UK Geenevasen, J Koomen, GJ
Citation
M. Madre et al., Purine nucleoside analogues. 11. An alternative synthesis of N- and O-alkyl derivatives of 9-and 7-[(2-acetoxyethoxy)methyl]-N-2-acetylguanine, COLL CZECH, 64(4), 1999, pp. 685-695
Citations number
11
Categorie Soggetti
Chemistry
Journal title
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
ISSN journal
00100765 → ACNP
Volume
64
Issue
4
Year of publication
1999
Pages
685 - 695
Database
ISI
SICI code
0010-0765(199904)64:4<685:PNA1AA>2.0.ZU;2-9
Abstract
Alkylations of 9- and 7-[(2-acetoxyethoxy)methyl]-N-2-acetylguanine with al kyl halogenides in the presence of base have been investigated affording a new route to the preparation of 1,N-2-dimethyl- as well as O-6-benzyl-9(7)- alkoxyalkylguanines. H-1 NMR spectra revealed that the 1,N-2-dimethyl deriv atives exist as mixtures of two conformers at room temperature due to the r estricted rotation about the C2-N2 bond. These findings agreed with conform ational calculations.