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2 Polish Journal of Chemistry

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Synthesis of the Potential Mannosidase Inhibitor via 1,3-Dipolar Cycloaddition Involving Cyclic Nitrone and Unsaturated Chiral gamma-Lactone

Stecko S., Paśniczek , K., Jurczak M., Solecka J., Chmielewski M.

Polish Journal of Chemistry

2009

Vol. 83, nr 2

237-243

The 1,3-dipolar cycloaddition of cyclic nitrone derived from tartaric acid with (S)-5-hydroxymethyl-2(5H)-furanone leads to a single adduct which was transformed into 1,2,6,7-tetrahydroxy-2-hydroxymethyl-indolizidine via reaction sequence involving protection of the hydroxymethyl group, reduction of the lactone moiety, protection of the resulting diol, and the N-O hydrogenolysis followed by the intramolecular alkylation of the nitrogen atom.

Synthesis of Iminosugars from alfa,beta-Unsaturated Lactones and N-Benzyl Nitrone

Panfil I., Urbańczyk-Lipkowska Z., Chmielewski M.

Polish Journal of Chemistry

2005

Vol. 79 / nr 2

239-249

1,3-Dipolar cycloadditions of N-benzyl nitrone 12 to D-glycero _-lactone 13 and to D-threo _-lactone 14 proceed with excellent stereoselectivity to provide only one adduct in each case, 16 and 17, respectively. The same reaction performed with L-erythro _-lactone 15 afforded two stereoisomers 18 and 19 in the ratio ca. 2.5:1. Cycloadducts 16-19 were subsequently subjected to a sequence of reactions involving hydrogenolysis of the N-O bond and intramolecular alkylation of the nitrogen atom by C-4 or C-5 carbon atom of the sugar backbone to afford 1,2-dideoxy iminosugars 25, 31, 38, 44 and 50 with a protected hydroxymethyl group at C-2 carbon atom.