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α-Selective Glucosylation Can Be Achieved with 6- O- para-Nitrobenzoyl Protection

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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.

OriginalsprogEngelsk
TidsskriftJournal of Organic Chemistry
Vol/bind87
Nummer21
Sider (fra-til)13763-13789
Antal sider27
ISSN0022-3263
DOI
StatusUdgivet - 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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