Synthesis of L-trehalose and observations on isomer and by-product formation

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With a view to gaining evidence on the mechanism by which D-trehalose is able to stabilise biomolecules towards dehydration (anhydrobiosis) and heat, L-trehalose has been prepared in order to allow comparative studies to be made. Little change can be induced in the ratio of the α,α-, α,β-, β,β-1,1′-stereoisomers of the disaccharide formed from 2,3,4,6-tetra-O-benzyl-L-glucose by using different reaction procedures and by varying the reaction conditions. Benzyl 2,3,4,6-tetra-O-benzyl α- and β-L-glucopyranoside are by-products in the trimethylsilyl trifluoromethanesulphonate mediated formation of the 1,1′-linked disaccharides.

Original languageEnglish
Pages (from-to)813-818
Number of pages6
JournalCarbohydrate Research
Issue number9
Publication statusPublished - 22 Apr 2003


  • 1,1′-Linked disaccharide
  • Anhydrobiosis
  • Biostabilisation
  • L-Trehalose

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