Open Glycoscience

2008, 1 : 19-24
Published online 2008 May 30. DOI: 10.2174/1875398100801010019
Publisher ID: TOGLYJ-1-19

How to Improve Chemical Synthesis of Laminaribiose on a Large Scale

F. Jamoisa , F. Le Goffic , J.C. Yvin , D. Plusquellec and V. Ferrières
ENSCR Avenue du Général Leclerc 35700 Rennes, France.

ABSTRACT

Laminaribiose, which is the simplest β-(1,3)-glucan, is one of the most powerful agents able to increase germination. Its chemical synthesis was revised in detail starting from peracylated donors and easily available glucofuranose protected by acetal groups in the presence of appropriated catalyst and/or promoter. We particularly focused our attention on the nature of the Lewis acid generally required in glycosidic couplings. Finally, an interesting scale-up was performed which allowed us to prepare laminaribiose on a kilogram scale.

Keywords:

LaLaminaribiose, Glycosylation, Trichloroacetimidates, Thioglycosides, Lewis acid.