Preparation of an Advanced Intermediate for the Synthesis of Stable Analogues of Guanofosfocin | Zendy

George Tesmol G. | Zendy; Szolcsányi Peter | Zendy; Koenig Stefan G. | Zendy; Paterson Duncan E. | Zendy; Isshiki Yoshiaki | Zendy; Vasella Andrea | Zendy

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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.

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