Lipase-Catalyzed 1,6-Acylation of d-Mannitol

Peter J. Duggan; David G. Humphrey; Victoria McCarl

doi:10.1071/CH04040

RESEARCH ARTICLE

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Lipase-Catalyzed 1,6-Acylation of d-Mannitol

Peter J. Duggan ^A ^D , David G. Humphrey ^B and Victoria McCarl ^C

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, Monash University, Clayton VIC 3800, Australia.

^B CSIRO Forestry and Forest Products, Private Bag 10, Clayton South VIC 3169, Australia.

^C Centre for Green Chemistry, School of Chemistry, Monash University, Clayton VIC 3800, Australia.

^D Author to whom correspondence should be addressed (e-mail: peter.duggan@sci.monash.edu.au).

Australian Journal of Chemistry 57(8) 741-745 https://doi.org/10.1071/CH04040
Submitted: 17 February 2004 Accepted: 8 April 2004 Published: 10 August 2004

Abstract

The selective synthesis of 1,6-diacyl d-mannitols from 2,2,2-trifluoroethyl esters using transesterification, catalyzed by lipases, has been investigated, and the results have been compared with those obtained from a typical acid chloride procedure and a phenylboronic acid-assisted approach. Three commercially available lipases and five 2,2,2-trifluoroethyl esters were examined. In most cases, the yields obtained from the lipase reactions were superior to those produced from either of the other two methods.

Acknowledgments

This worked was funded by the Australian Research Council and Monash University. V.M. is a recipient of an Australian Postgraduate Award. Novo Nordisk A/S, Denmark, is acknowledged for its generous donation of Novozym 435, and Jessica Unthank is thanked for performing the transesterification with 12 on a larger scale.

References

Lipase-Catalyzed 1,6-Acylation of d-Mannitol

Abstract

Acknowledgments

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