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Molecules 2002, 7(5), 437-446; doi:10.3390/70500437
Article

Synthesis, Crystal Structure, and Conformation of Methyl 5-Oacetyl-5-cyano-6-deoxy-2,3-O-isopropylidene-β-L-gulofuranoside

1, 1, 1,* , 1, 2 and 3
1 Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-84238 Bratislava, Slovakia 2 Department of Inorganic Environmental Chemistry, Chalmers University of Technology, SE-41296 Göteborg, Sweden 3 Institute of Inorganic Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-84236 Bratislava, Slovakia
* Author to whom correspondence should be addressed.
Received: 14 November 2001 / Revised: 13 May 2002 / Accepted: 13 May 2002 / Published: 31 May 2002
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Abstract

Methyl 5-O-acetyl-5-cyano-6-deoxy-2,3-O-isopropylidene-β-L-gulofuranoside was prepared in high yield from methyl 6-deoxy-2,3-O-isopropylidene-α-D-lyxopentodialdo-1,4-furanoside. The configuration at the C5 atom was unambiguosly established by single crystal X-ray analysis of the corresponding 5-O-acetyl derivative. The conformation of the furanose and 1,3-dioxolane rings is also discussed.
Keywords: Saccharide cyanohydrins; methyl 2; 3-O-isopropylidene-β-L-gulofuranoside; Xray crystallography; conformation Saccharide cyanohydrins; methyl 2; 3-O-isopropylidene-β-L-gulofuranoside; Xray crystallography; conformation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Mičová, J.; Steiner, B.; Koóš, M.; Gajdoš, J.; Langer, V.; Gyepesová, D. Synthesis, Crystal Structure, and Conformation of Methyl 5-Oacetyl-5-cyano-6-deoxy-2,3-O-isopropylidene-β-L-gulofuranoside. Molecules 2002, 7, 437-446.

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