Title

Synthesis of a dimer of β-(1,4)-L-arabinosyl-(2S,4R)-4-hydroxyproline inspired by Art v 1, the major allergen of mugwort

Document Type

Article

Publication Date

11-5-2010

Abstract

Nα-tert-Butoxycarbonyl-L-trans-4-hydroxyproline allyl ester (Boc-Hyp-OAll) was glycosylated with 2,3,5-tri-O-benzyl-L-arabinose p-cresylthioglycoside in 60% yield with 4:1 β:α stereoselectivity. Deprotection of N- and C-terminii independently gave a prolyl amine and prolyl carboxylate respectively that were coupled under standard conditions with 1-[bis-(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5,b]-pyridininium hexafluorophosphate 3-oxide (N-HATU) to give the dimer 1 in 46% yield. These results represent the first steps toward the production of homogeneous oligomers to determine the minimal epitope of the Art v 1 allergen.

Publication Source (Journal or Book title)

Organic letters

First Page

4968

Last Page

71

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