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Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-101 Ookayama, Meguro, Japan
; Fax: +81-3-5734-2884
; Tel: +81-3-5734-2471
Org. Biomol. Chem., 2012,10, 9570-9582
01 Oct 2012,
17 Oct 2012
First published online
19 Oct 2012
In this paper, we describe an effective method for the elongation of a GlcNα(1,4)GlcAβ(1,4) sequence using a GlcNTrocα(1,4)GlcA disaccharide unit and the synthesis of the N- and/or O-sulfated GlcNα(1,4)GlcAβ(1,4) oligosaccharides. N-Troc protection of GlcNα(1,4)GlcA units was effective for the synthesis of the GlcNα(1,4)GlcAβ(1,4) oligosaccharides in comparison with the azido substituent. The GlcNα(1,4)GlcAβ(1,4) dodecasaccharide was successfully prepared by the direct β-selective glycosidation of glucuronate in the GlcNα(1,4)GlcAβ(1,4)GlcNα(1,4)GlcAβ(1,4) tetrasaccharide. In addition, the synthesis of the N- and/or O-sulfated GlcNα(1,4)GlcAβ(1,4) oligosaccharides was accomplished by fluorous-assisted deprotection and sulfation. The fluorous-assisted synthetic technology applied to the highly polar sulfated oligosaccharide permits it to be more easily separated from the highly polar reagents, such as SO3·NEt3.
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Organic & Biomolecular Chemistry
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