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- Steiner, Bohumil, et al.
(författare)
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Cyanohydrins from methyl 6-deoxy-2,3-O-isopropylidene-alpha-L-lyxo-hexofuranosid-4-ulose via Bucherer-Bergs and Strecker reactions
- 2013
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Ingår i: Carbohydrate Research. - : Elsevier BV. - 0008-6215 .- 1873-426X. ; 369, s. 31-37
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Tidskriftsartikel (refereegranskat)abstract
- The formation of methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-alpha-L-talopyranoside (3), methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-alpha-L-mannopyranoside (4), methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-beta-D-allopyranoside (5), and methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-beta-D-gulopyranoside (7) from methyl 6-deoxy-2,3-O-isopropylidene-alpha-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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