Cyanohydrins from methyl 6-deoxy-2,3-O-isopropylidene-alpha-L-lyxo-hexofuranosid-4-ulose via Bucherer-Bergs and Strecker reactions
Journal article, 2013

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.

conformation

molecular-structure

Cyanohydrins

crystal

lewis-acid

Bucherer-Bergs hydantoin synthesis

derivatives

Strecker synthesis

Carbohydrates

biology

Kiliani

sugar amino-acids

Author

Bohumil Steiner

Slovak Academy of Sciences

Vratislav Langer

Chalmers, Chemical and Biological Engineering, Environmental Inorganic Chemistry

M. Bella

Slovak Academy of Sciences

Miroslav Koos

Slovak Academy of Sciences

Carbohydrate Research

0008-6215 (ISSN)

Vol. 369 31-37

Subject Categories

Biochemistry and Molecular Biology

DOI

10.1016/j.carres.2012.09.008

More information

Created

10/8/2017