Simple formylacetal (CH2) as a novel linker for saccharide synthesis on soluble-polymer support |
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Authors: | Masato Oikawa Tatsushi Tanaka Makoto Sasaki |
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Institution: | a Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Tsutsumidori-Amamiya, Aoba-ku, Sendai 981-8555, Japan b Department of Chemistry, Graduate School of Science, Osaka University, Machikaneyama-cho 1-1, Toyonaka, Osaka 560-0043, Japan |
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Abstract: | Described herein is a new formylacetal (CH2) linker for immobilization of small molecules onto a soluble-polymer support, poly(ethylene glycol) ω-monomethyl ether (MPEG), and its application to saccharide synthesis. This small linker allows immobilization of a hindered hydroxy group such as the 4-hydroxy group of glucose onto MPEG. The linker is stable under several reaction conditions including glycosylation. Removal of this support was found to be achieved through cleavage of the CH2 linker either by a Lewis acid (TMSI or Ce(OTf)x) or a Brønsted acid (trifluoroacetic acid) in moderate to good yields. In combination with solid acid catalyst, simpler operations became possible during the working-up and purification processes. |
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