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Synfacts 2006(12): 1297-1297
DOI: 10.1055/s-2006-955623
DOI: 10.1055/s-2006-955623
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
Polymer-Assisted Strategy for Deprotection of Protected Sugars
H. Tanaka, T. Ishida, N. Matoba, H. Tsukamoto, H. Yamada, T. Takahashi*
Tokyo Institute of Technology, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200612/lookinside/thumbnails/10.1055-s-2006-955623-1.jpg)
Significance
An efficient method for the deprotection of protected oligosaccharides based on a polymer-assisted strategy was developed. Thus, treatment of methyl 2,3,4-O-tribenzylglucoside (1) with a prelinker 2 (1.2 equiv) under acidic conditions gave the protected glucoside 3. The subsequent amidation of 3 with an ArgoPore resin-supported amine 4 (3.0 equiv) afforded the solid-supported protected glucose 5 in 99% in two steps. The removal of benzyl ethers by Birch reduction and the subsequent acidic treatment gave the α-methyl glucoside 5 in 91% overall yield from 1. This strategy was applied to the synthesis of dimeric and trimeric Lewis X derivatives (7 and 8).