Glycosylations Directed by the Armed-Disarmed Effect with Acceptors Containing a Single Ester Group

A selective glycosylation reaction controlled by the armed‐disarmed effect is described by the use of phenyl thioglycosides. The donor thioglycoside is fully protected with benzyl ethers while the acceptor thioglycoside contains benzyl ethers at position 2 and 3 and a strongly electron‐withdrawing p...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-08, Vol.2007 (23), p.3935-3941
Main Authors: Schmidt, Thomas H., Madsen, Robert
Format: Article
Language:English
Subjects:
Armed-disarmed effect
Carbohydrates
Glycosylation
Protecting groups
Tandem reactions
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Summary:A selective glycosylation reaction controlled by the armed‐disarmed effect is described by the use of phenyl thioglycosides. The donor thioglycoside is fully protected with benzyl ethers while the acceptor thioglycoside contains benzyl ethers at position 2 and 3 and a strongly electron‐withdrawing pentafluorobenzoate ester group at position 6. The coupling can be performed with galactose, glucose, mannose, and phthalimide‐protected glucosamine to afford the corresponding 1,4‐linked disaccharides in good yield. These disaccharides can act as glycosyl donors for an additional coupling reaction in the same pot if another acceptor and more promoter are added. In this way, two consecutiveglycosylations can be achieved to afford trisaccharides in one operation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700347