A general route to pendant C-glycosyl 1,2- and 1,3-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.
Inaba
Yoko
Y
Division of Functional Material Science, Nara Women's University, Nara, Japan.
Fujimoto
Tomomi
T
Ono
Hiroshi
H
Obata
Makoto
M
Yano
Shigenobu
S
Mikata
Yuji
Y
D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure
D003959:Diamines; D006027:Glycosides