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

doi:10.3390/70500437

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

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

Júlia Mičová¹, Bohumil Steiner¹, Miroslav Koóš^1,* , Ján Gajdoš¹, Vratislav Langer² and Dalma Gyepesová³

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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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(5):437-446.

Chicago/Turabian Style

Mičová, Júlia; Steiner, Bohumil; Koóš, Miroslav; Gajdoš, Ján; Langer, Vratislav; Gyepesová, Dalma. 2002. "Synthesis, Crystal Structure, and Conformation of Methyl 5-Oacetyl-5-cyano-6-deoxy-2,3-O-isopropylidene-β-L-gulofuranoside." Molecules 7, no. 5: 437-446.

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