| DOI | Resolve DOI: https://doi.org/10.1016/j.tet.2011.05.133 |
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| Author | Search for: Yu, Siu Hong1; Search for: Whitfield, Dennis M. |
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| Affiliation | - National Research Council of Canada. NRC Institute for Biological Sciences
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| Format | Text, Article |
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| Subject | protecting group; glycolipid; glycopeptide; oligosaccharide |
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| Abstract | A pragmatic approach for preparing glycoconjugates of complex oligosaccharides is to prepare the oligosaccharide as a building block with most of its protecting groups exchanged to protecting groups whose cleavage and other manipulations are highly compatible with the functional groups of complex aglycones. For such an approach the reducing end sugar of the building bloc must be protected with a cleavable protecting group during the oligosaccharide synthesis.We demonstrate that the acid labile 1- methyl 10-cyclopropylmethyl (MCPM) can be effectively used for this purpose. A trisaccharide glycolipid and a disaccharide glycoamino acid are prepared. The absolute chirality of the MCPM in one key acceptor is determined by a combination of NMR NOE measurements, DFT molecular modeling and Noyori catalyst catalyzed asymmetric reduction. |
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| Publication date | 2011-06-13 |
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| In | |
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| Language | English |
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| Peer reviewed | Yes |
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| NPARC number | 19254213 |
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| Export citation | Export as RIS |
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| Report a correction | Report a correction (opens in a new tab) |
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| Record identifier | 290a842d-02a5-4879-a655-7786fc98350d |
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| Record created | 2012-03-08 |
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| Record modified | 2020-04-21 |
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