| Author | Search for: Whitfield, D. M.1 |
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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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| Conference | 239th ACS National Meeting & Exposition American Chemical Society Meeting, March 21-25, 2010; San Francisco, CA, USA |
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| Abstract | [During density functional theory (DFT) studies of glycopyranosyl oxacarbenium ions two unexpected conformational preferences for substituents at O-2 were discovered. One is that substituents at O-2 have a propensity to be equatorial. This leads to a unexpected stability of the 5S1 conformer of D-glucopyranosyl oxacarbenium ions. The second is for the first atom attached to O-2 to adopt a syn conformation. This was shown to be a result of hyperconjugation between a lone pair on O-2 and the LUMO associated with the C-1--O-5 double bond. In order to provide experimental corroboration we have prepared glucopyranosyl donors with a chiral methyl cyclopropylmethyl group at O-2. The results of glycosylation reactions with 4 glycosyl acceptors of these donors will be presented. As well, the conformational preferences of the associated glucopyranosyl oxacarbenium ions as determined by DFT calculations will be presented]> |
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| Publication date | 2010-04-01 |
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| In | |
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| Language | English |
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| Peer reviewed | Yes |
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| NPARC number | 17438027 |
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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 | b450c2d4-ff3c-4722-8157-2b5c7bab59fa |
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| Record created | 2011-04-05 |
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| Record modified | 2020-04-17 |
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