Synthesis, Crystal Structure, and Conformation of Methyl 5-Oacetyl-5-cyano-6-deoxy-2,3-O-isopropylidene-β-L-gulofuranoside
Received: 14 November 2001 / Revised: 13 May 2002 / Accepted: 13 May 2002 / Published: 31 May 2002
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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.