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

Author(s): Júlia Mičová | Bohumil Steiner | Miroslav Koóš | Ján Gajdoš | Vratislav Langer | Dalma Gyepesová

Journal: Molecules ISSN 1420-3049
Volume: 7; Issue: 5; Start page: 437; Date: 2002;
Original page

Keywords: Saccharide cyanohydrins | methyl 2 | 3-O-isopropylidene-β-L-gulofuranoside | Xray crystallography | conformation

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.