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α-Selective Glucosylation Can Be Achieved with 6- O- para-Nitrobenzoyl Protection
Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review
DOI
- https://doi.org/10.1021/acs.joc.2c01475
Forlagets udgivne version
- Helle H. Trinderup
- Line Juul-Madsen
- Laura Press
- Michael Madsen ,
- Henrik H. Jensen
A systematic study of the effect of various 6-O-acyl groups on anomeric selectivity in glucosylations with thioglycoside donors was conducted. All eight different esters were found to induce moderate-to-high α-selectivity in glucosylation with l-menthol with the best being 6-O-p-nitrobenzoyl. The effect appears to be general across various glucosyl acceptors, glucosyl donor types, and modes of activation. No evidence was found in favor of distal participation.
| Originalsprog | Engelsk |
|---|---|
| Tidsskrift | Journal of Organic Chemistry |
| Vol/bind | 87 |
| Nummer | 21 |
| Sider (fra-til) | 13763-13789 |
| Antal sider | 27 |
| ISSN | 0022-3263 |
| DOI | |
| Status | Udgivet - nov. 2022 |
Bibliografisk note
Funding Information:
We are grateful to Independent Research Fund Denmark and the Novo Nordisk Foundation for financial support and to Drs Peter Nørby and Jacob Overgaard for technical assistance with obtaining the X-ray crystal structure of 55 .
Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
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