Abstract
The conformations of the
methyl 2,3,4,6-tetra-O-acetyl-5-hexulosonates have been determined by analysis of their
N.M.R. spectra. The arabino
and lyxo
isomers are preponderantly in the planar zig-zag form,
whereas in the xylo and ribo isomers rotation around the
C2-C3 or C3-C4 bond had occurred to a gauche
arrangement in order to relieve the steric interaction (in the zig-zag form) between the acetoxy groups on C2 and C4. The
location of the gauche arrangement
depends on the size of the groups attached to C2 and C4. Acylated
derivatives of keto-D-fructose,
keto-L-sorbose,
and keto-D-psicose
have similar conformations.
Cited by
34 articles.
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1. Stephen John Angyal 1914–2012;Historical Records of Australian Science;2015
2. Stephen John Charles Angyal;Advances in Carbohydrate Chemistry and Biochemistry;2013
3. Activation of Carbonyl-Containing Molecules with Solid Lewis Acids in Aqueous Media;ACS Catalysis;2011-10-17
4. Isolation and identification of the intermediates during pyrazole formation of some carbohydrate hydrazone derivatives;Carbohydrate Research;2000-05
5. Synthesis and conformational analysis of seco C-nucleosides and their diseco double-headed analogues of the 1,2,4-triazole, 1,2,4-triazolo[3,4-b]1,3,4-thiadiazole1Parts of this work were presented at 19th International Carbohydrate Symposium, San Diego, CA, USA, August 1998 and XIII International Round Table, Nucleosides, Nucleotides and their Biological Applications, Montpellier, France, September 1998.1;Carbohydrate Research;1998-11