Synthesis of a C-galactopyranosyl-linked N-substituted 1,2-ethylenediamine.
Center of Excellence for Innovation in Chemistry (PERCH-CIC), Department of Chemistry, Faculty of Science, Mahasarakham University, Mahasarakham, Thailand. uthai.s@msu.ac.th
Carbohydrate research 2010 Jun 16A 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. Copyright (c) 2010 Elsevier Ltd. All rights reserved.
Citation
Uthai Sakee, Chiradet Nasuk. Synthesis of a C-galactopyranosyl-linked N-substituted 1,2-ethylenediamine. Carbohydrate research. 2010 Jun 16;345(9):1222-4
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PMID: 20427036
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