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Synfacts 2005(0): 0087-0087  
DOI: 10.1055/s-2005-869887
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Polymeric DBU for Preparation of Glycosyl Trichloroacetimidates

Contributor(s): Yasuhiro Uozumi, Tomohiko Beppu
J. L. Chiara*, L. Encinas, B. Díaz
CSIC, Madrid, Spain
A Study of Polymer-Supported Bases for the Solution Phase Synthesis of Glycosyl Trichloroacetimidates
Tetrahydron Lett.  2005,  46:  2445-2448  
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Publication History

Publication Date:
20 July 2005 (online)

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Key words

carbohydrates - solid-supported reagents - glycosylation

Significance

The facile and practical procedure for preparation of glycosyl trichloroacetimidates was developed by using polystyrene-supported bases (5 substrates and 23 reaction conditions were examined). PS-DBU was proved to be the most efficient base in this protocol. The reactions of 2,3,4,6-tetra-acyloxy-α-d-glucopyranose derivatives (R = Ac or Bz) with trichloroacetonitrile proceeded smoothly in the presence of PS-DBU to give the corresponding α-anomers in quantitative yields. The trichloroacetimidates (α-anomers) were isolated without any chromatographic purification.

Comment

Accelerated synthesis of glycoconjugates promises to greatly impact the emerging field of glycomics. This polymer-supported protocol realized complete removal of the traces of base from the products.

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