A general route to pendant C-glycosyl 1,2- and 1,3-diamines

作者：Inaba Yoko; Fujimoto Tomomi; Ono Hiroshi; Obata Makoto; Yano Shigenobu; Mikata Yuji^*

来源：Carbohydrate Research, 2008, 343(5): 941-950.

DOI：10.1016/j.carres.2008.01.030

• C-glycosyl compounds
• diamines
• branched C-glycosyl diamines

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.

• 出版日期2008-4-7