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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

B. Steiner ; Vratislav Langer (Institutionen för kemi- och bioteknik, Oorganisk miljökemi) ; M. Bella ; M. Koos
Carbohydrate Research (0008-6215). Vol. 369 (2013), p. 31-37.
[Artikel, refereegranskad vetenskaplig]

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.

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



Denna post skapades 2013-04-05.
CPL Pubid: 175363

 

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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Oorganisk miljökemi (2005-2014)

Ämnesområden

Biokemi och molekylärbiologi

Chalmers infrastruktur