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Total synthesis of 2‐(β‐ D ‐ribofuranosyl)thiazole‐4‐carboxamide (Tiazofurin) and of precursors of ribo ‐ C ‐nucleosides
Author(s) -
Bimwala R. Mampuya,
Vogel Pierre
Publication year - 1989
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.19890720819
Subject(s) - chemistry , tris , benzamide , imidazolidine , stereochemistry , thiazole , carboxamide , medicinal chemistry , biochemistry
(1 R ,2 S ,4 R )‐2‐Cyano‐7‐oxabicyclo[2.2.1]hept‐5‐en‐2‐yl (1 S ′)‐camphanate ( 5 ) was transformed into (−)‐methyl 2,5‐anhydro‐3,4,6‐ O ‐tris[( tert ‐butyl)dimethylsilyl]‐ D ‐allonate ( 2 ), (+)‐1,3‐diphenyl‐2‐{2′,3′,5′‐ O ‐tris[( tert ‐butyl)dimethylsilyl]‐β‐ D ‐ribofuranosyl}imidazolidine ( 3 ), and the benzamide 20 of 1‐amino‐2,5‐anhydro‐1‐deoxy‐3,4,6‐ O ‐tris‐[(( tert ‐butyl)dimethylsily)]‐ D ‐allitol. Compound 2 was converted efficiently into optically active tiazofurin ( 1 ).