Unusual Glycosylation of 9-O-Benzylallosamizoline

Regine Blattner; Richard H. Furneaux; Graeme J. Gainsford; Herbert Wong

doi:10.1071/CH03167

RESEARCH ARTICLE

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Unusual Glycosylation of 9-O-Benzylallosamizoline

Regine Blattner ^A ^B , Richard H. Furneaux ^A , Graeme J. Gainsford ^A and Herbert Wong ^A

+ Author Affiliations

- Author Affiliations

^A Industrial Research Ltd, PO Box 31-310, Lower Hutt, New Zealand.

^B Author to whom correspondence should be addressed (e-mail: r.blattner@irl.cri.nz).

Australian Journal of Chemistry 57(8) 799-802 https://doi.org/10.1071/CH03167
Submitted: 30 June 2003 Accepted: 12 August 2003 Published: 10 August 2004

Abstract

Intended selective glycosylation of the 9-O-benzyl ether 4 of allosamizoline 1 with a slight molar excess of 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-d-glucopyranosyl trichloroacetimidate 6 unexpectedly gave the di-O-glycosylated product 5 in high yield. In its crystalline form, this diglycoside adopts a conformation with the sugar rings extended away from the bicyclic unit of the aglycon and from each other. NMR spectroscopic features indicate that this conformation is not retained in solution.

Acknowledgments

The University of Canterbury Crystallography Laboratory is thanked for carrying out the X-ray data collection, and Clas Landersjo is thanked for assistance with aspects of the NMR work. Robin Ferrier’s help is also acknowledged.

References

Unusual Glycosylation of 9-O-Benzylallosamizoline

Abstract

Acknowledgments

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