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Cyanohydrins from m...
Cyanohydrins from methyl 6-deoxy-2,3-O-isopropylidene-alpha-L-lyxo-hexofuranosid-4-ulose via Bucherer-Bergs and Strecker reactions
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- Steiner, Bohumil (author)
- Slovak Academy of Sciences
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- Langer, Vratislav, 1949 (author)
- Chalmers tekniska högskola,Chalmers University of Technology
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- 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.
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In: Carbohydrate Research. - : Elsevier BV. - 0008-6215 .- 1873-426X. ; 369, s. 31-37
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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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