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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.