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Isonucleosides with Exocyclic Methylene Groups
Author(s) -
Bera Sanjib,
Nair Vasu
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000705)83:7<1398::aid-hlca1398>3.0.co;2-i
Subject(s) - chemistry , methylene , nucleobase , pyrimidine , moiety , sugar , mitsunobu reaction , stereochemistry , methylene bridge , medicinal chemistry , organic chemistry , dna , biochemistry
Synthesis of isonucleosides 13 , 14 , 16 , and 17 , bearing an exocyclic methylidene group at the sugar moiety, starting from a 3‐keto sugar is described. The keto compound was converted to the methylene‐sugar 10b ( Scheme 1 ), which was coupled with nucleobases by means of the Mitsunobu reaction. The coupling reaction with adenine and 8‐azaadenine produced both the N 9 ‐ and N 3 ‐nucleosides (see 13 and 14 , resp.; Scheme 2 ). The structures of 13a and 14a were confirmed by single‐crystal X‐ray data. Synthesis of the pyrimidine compounds was also approached from the β ‐amino sugar 20 that was prepared using a Gabriel ‐synthesis methodology ( Scheme 3 ).