Synthesis of 1′‐Homo‐N‐nucleosides from Hexitols | Zendy

Saladino Raffaele | Zendy; Ciambecchini Umberto | Zendy; Hanessian Stephen | Zendy

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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)

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