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A convenient synthesis of new 6-substituted purinylcarbanucleosides on cyclopenta[b]thiophene
Published: 29 November 2008 by MDPI in The 12th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic Chemistry and Natural Products
Abstract: The first members of a new family of heterocarbobicyclic nucleoside analogues have been synthesized from the cis/trans mixture of (4-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl)methanols cis/trans-7. The separation of cis and trans intermediates during preparation of the 6-chloropurine derivatives allowed separate preparation of the purine heterocarbanucleosides cis-10 and trans-11, from which cis-(12-14) and trans-(16-18) were obtained by replacement of the 6-chloro substituent with amino, hydroxy and cyclopropylamino groups. Additionally, the 6-phenyl-purinyl analogues cis-15 and trans-19 were prepared from cis-10 and trans-11 using Suzuki-Miyaura methodology.