Cyanohydrins from methyl 6-deoxy-2,3-O-isopropylidene-α-l-lyxo-hexofuranosid-4-ulose via Bucherer–Bergs and Strecker reactions

Add time:09/10/2019    Source:sciencedirect.com

The formation of methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-α-l-talopyranoside (3), methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-α-l-mannopyranoside (4), methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-β-d-allopyranoside (5), and methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-β-d-gulopyranoside (7) from methyl 6-deoxy-2,3-O-isopropylidene-α-l-lyxo-hexopyranosid-4-ulose (1) under Strecker amino nitrile synthesis and Bucherer–Bergs hydantoin synthesis reaction conditions, respectively, is reported. Their structures were determined on the basis of NMR and mass spectral data. The configurations of free cyanohydrins 3 and 4 and 4-O-acetylated cyanohydrins 6 and 8 (obtained by acetylation of 5 and 7, respectively) were established by single-crystal X-ray analysis. The conformations of the six-membered pyranose ring and five-membered 1,3-dioxolane ring in compounds 3, 4, 6, and 8 are also reported.

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