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Synthesis of 1′‐Homo‐N‐nucleosides from Hexitols
Author(s) -
Saladino Raffaele,
Ciambecchini Umberto,
Hanessian Stephen
Publication year - 2003
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.200300328
Subject(s) - chemistry , d mannitol , thymine , epoxide , uracil , nucleophile , catalysis , stereochemistry , nucleic acid , organic chemistry , mannitol , dna , biochemistry
This paper describes a new route for the synthesis of N ‐(1′‐homo‐ L ‐gulitol)nucleosides and amino sugar analogues of N ‐(1′‐homo‐ L ‐gulitol)nucleosides by nucleophilic epoxide ring‐opening followed by O ‐heterocyclization of 1,2:5,6‐dianhydro‐3,4‐di‐ O ‐benzyl‐ D ‐mannitol and 1,2:5,6‐dianhydro‐3,4‐diazido‐ D ‐iditol, respectively. Magnesium perchlorate [Mg(ClO 4 ) 2 ] was found to be the best catalyst for the reaction of silylated bases, derived from uracil, thymine and adenine, with these bis(epoxides). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)