Premium
Preparation of an Advanced Intermediate for the Synthesis of Stable Analogues of Guanofosfocin
Author(s) -
George Tesmol G.,
Szolcsányi Peter,
Koenig Stefan G.,
Paterson Duncan E.,
Isshiki Yoshiaki,
Vasella Andrea
Publication year - 2004
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/hlca.200490118
Subject(s) - chemistry , guanosine , moiety , guanine , nucleoside , stereochemistry , nucleotide , combinatorial chemistry , biochemistry , gene
The synthesis of C ‐mannosyl‐guanosine 23 , an advanced intermediate for the preparation of stable analogues of guanofosfocin, is described. This convergent approach features an improved Traube ‐type synthesis of a 8‐substituted guanine, followed by ribosylation. NMR Studies show that the C ‐mannopyranosyl moiety of 23 adopts a distorted 1 C 4 conformation while the nucleoside is predominantly syn ‐oriented.