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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

Steiner, Bohumil (author)
Slovak Academy of Sciences
Langer, Vratislav, 1949 (author)
Chalmers tekniska högskola,Chalmers University of Technology
Bella, M. (author)
Slovak Academy of Sciences
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Koos, Miroslav (author)
Slovak Academy of Sciences
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 (creator_code:org_t)
Elsevier BV, 2013
2013
English.
In: Carbohydrate Research. - : Elsevier BV. - 0008-6215 .- 1873-426X. ; 369, s. 31-37
  • Journal article (peer-reviewed)
Abstract Subject headings
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  • 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.

Subject headings

NATURVETENSKAP  -- Biologi -- Biokemi och molekylärbiologi (hsv//swe)
NATURAL SCIENCES  -- Biological Sciences -- Biochemistry and Molecular Biology (hsv//eng)

Keyword

crystal
molecular-structure
derivatives
conformation
Bucherer-Bergs hydantoin synthesis
Cyanohydrins
sugar amino-acids
Kiliani
biology
Strecker synthesis
Carbohydrates
lewis-acid

Publication and Content Type

art (subject category)
ref (subject category)

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