Reaction of anhydro sugars with sodium cobalt tetracarbonyl and carbon monoxide
Author(s) -
Alex Rosenthal,
J. N. C. Whyte
Publication year - 1968
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v68-364
Subject(s) - chemistry , cobalt , methanol , ether , carbon monoxide , sodium , medicinal chemistry , yield (engineering) , organic chemistry , inorganic chemistry , catalysis , materials science , metallurgy
5,6-Anhydro-1,2-O-isopropylidene-α-D-glucofuranose reacts with sodium cobalt tetracarbonyl and carbon monoxide in methanol to afford methyl 6-deoxy-1,2-O-isopropyhdene-α-D-gluco-heptofuranouronate (3) in 82% yield. Treatment of tri-O-acetyl-1,2-anhydro-D-glucopyranose with sodium cobalt tetracarbonyl in ether gives 3,4,6-tri-O-acetyl-D-glucal. The 2,3-anhydro sugars are resistant to cleavage by cobalt tetracarbonyl anion in ether or in methanol. Sugar acetates are de-O-acetylated by treatment with sodium cobalt tetracarbonyl in ether–methanol.
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