A general route to pendant C-glycosyl 1,2- and 1,3-diamines |
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Authors: | Inaba Yoko Fujimoto Tomomi Ono Hiroshi Obata Makoto Yano Shigenobu Mikata Yuji |
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Affiliation: | Division of Functional Material Science, Nara Women's University, Nara, Japan. |
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Abstract: | Practical and convenient preparations of C-glycosyl 1,2- and 1,3-alkanediamines are described. Two 1,2-ethylenediamine derivatives were synthesized from acetylated allyl alpha-C-glycosyl compounds via dibromination, azidation, carbohydrate deprotection, and azide reduction. Four 1,3-propanediamine derivatives were prepared from acetylated sugar halides via C-glycosylation with sodiomalononitrile, followed by the reduction of the nitrile moieties and the deacetylation of the carbohydrate moiety. These 1,3-propanediamine derivatives have the beta-anomeric configurations. The methods reported here serve as general routes to access carbohydrate-diamine conjugates with C-glycosyl linkages. |
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Keywords: | C-Glycosyl compounds Diamines Branched C-glycosyl diamines |
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