Synthesis of a C-galactopyranosyl-linked N-substituted 1,2-ethylenediamine.
A straightforward route to a C-galactopyranosyl-linked 1,2-ethylenediamine is described. The five-step synthetic procedure involves: (i) C-allenylation of D-galactopyranose pentaacetate with propargyl trimethylsilane in the presence of a Lewis acid, (ii) iodination of allenyl galactopyranosyl tetraacetate to diiodoallyl galactopyranosyl tetraacetate, (iii) displacement of the allylic iodide with N-Boc-ethylenediamine, (iv) catalytic hydrogenation of vinyl iodide to alkane, (v) deprotection of the acetyl and N-Boc-groups using acid-catalyzed hydrolysis. This method demonstrates a general method to access a new class of carbohydrate-ethylenediamine C-glycosyl chelators.
Sakee
Uthai
U
Center of Excellence for Innovation in Chemistry (PERCH-CIC), Department of Chemistry, Faculty of Science, Mahasarakham University, Mahasarakham, Thailand. uthai.s@msu.ac.th
Nasuk
Chiradet
C
D005029:Ethylenediamines / Q000138:chemical synthesis* / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
D005029:Ethylenediamines; D006027:Glycosides; D009584:Nitrogen; D005690:Galactose