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Influence of the N 3‐Protection Group on N 1‐ vs. O 2 ‐Alkylation in the Mitsunobu Reaction
Author(s) -
Ludek Olaf R.,
Meier Chris
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500801
Subject(s) - chemistry , alkylation , thymine , regioselectivity , mitsunobu reaction , group (periodic table) , nucleoside , stereochemistry , protecting group , grignard reaction , medicinal chemistry , organic chemistry , catalysis , reagent , dna , biochemistry , alkyl
The influence of the N 3‐protection group of thymine on the regioselectivity of the N 1‐ vs. O 2 ‐alkylation under Mitsunobu conditions is described. A series of N 3‐protected thymine derivatives 8a – f was prepared and coupled to cyclopentanol as model compound for carbocyclic nucleoside precursors. Finally, the N 3‐BOM group was selected to improve our previously reported synthetic strategy to carbocyclic thymidine ( carba ‐dT). Moreover, the 2,6‐dimethyl‐Bz group led exclusively to the O 2 ‐analogue of carba ‐dT. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)