Synthesis of 2‐carbamoylmethyl‐6‐β‐D‐ribofuranosylpyridine with the aid of a Pd(0)‐catalyzed reaction | Zendy

De Vos Eric | Zendy; Esmans Eddy L. | Zendy; Alderweireldt Frank C. | Zendy; Balzarini Jan | Zendy; De Clercq Erik | Zendy

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Synthesis of 2‐carbamoylmethyl‐6‐β‐D‐ribofuranosylpyridine with the aid of a Pd(0)‐catalyzed reaction

Author(s) -

De Vos Eric,

Esmans Eddy L.,

Alderweireldt Frank C.,

Balzarini Jan,

De Clercq Erik

Publication year - 1993

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570300513

Subject(s) - chemistry , reagent , pyridine , catalysis , triphenylphosphine , palladium , medicinal chemistry , polymer chemistry , organic chemistry

D‐Allo/D‐altro‐2‐(2,4:3,5‐di‐ O ‐benzylidenepentitol‐l‐yl)‐6‐ethoxycarbonylmethylpyridine was synthesized from 2‐bromo‐6‐(2,4:3,5‐di‐ O ‐benzylidenepentitol‐1‐yl)pyridine or 2‐(2,4:3,5‐di‐ O ‐benzylidenepentitol‐1‐yl)‐6‐iodopyridine by means of a tetrakis(triphenylphosphine)palladium(O)‐catalyzed reaction with Reformatsky's reagent. Subsequent ammonolysis and mesylation of the D‐altro‐ethoxycarbonylmethyl compound gave D‐altro‐2‐carbamoylmethyl‐6‐(1‐ O ‐mesyl‐2,4:3,5‐di‐ O ‐benzylidenepentitol‐l‐yl)pyridine which was cyclized to 2‐carbamoylmethyl‐6‐β‐D‐ribofuranosylpyridine.

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