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

• Autorzy: Panfil I. , Urbańczyk-Lipkowska Z. , Chmielewski M.
• Języki publikacji: EN

Abstrakty

EN

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.

Słowa kluczowe

EN

unsaturated aldono-1,5-lactones; 1,3-dipolar cycloadditions; iminosugars

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 2
• Strony: 239--249
• Opis fizyczny: Bibliogr. 28

Twórcy

autor

Panfil I.

• Institute of Organic Chemistry of the Polish Academy of Sciences, 01-224 Warsaw, Kasprzaka 44/52, Poland

autor

Urbańczyk-Lipkowska Z.

• Institute of Organic Chemistry of the Polish Academy of Sciences, 01-224 Warsaw, Kasprzaka 44/52, Poland

autor

Chmielewski M.

• Institute of Organic Chemistry of the Polish Academy of Sciences, 01-224 Warsaw, Kasprzaka 44/52, Poland

• Institute of Organic Chemistry of the Polish Academy of Sciences, 01-224 Warsaw, Kasprzaka 44/52, Poland

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