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PubMed · 12433461

Solution- and solid-phase oligosaccharide synthesis using glucosyl iodides: a comparative study.

Son N Lam·Jacquelyn Gervay-Hague
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Abstract

Glycosyl iodide donors have been used in both solid- and solution-phase syntheses yielding alpha-(1 --> 6)-linked glucosyl oligomers in highly efficient protocols. While the solid-phase strategy offers advantages in terms of ease of purification, it requires a total of 7.5 equiv of donor and approximately 12 h to complete the incorporation of one monosaccharide unit. In contrast, solution-phase methods require only 2.5 equiv of donor and 2-3 h reaction time per glycosylation. Moreover, since the reactions are virtually quantitative (> 90%) column chromatography of the material is facile. The overall advantages of solution-phase oligosaccharide synthesis were further illustrated in the convergent synthesis of a hexamer (methoxycarbonylmethyl 6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-glucopyranosyl-(1 --> 6)-tetrakis-(2,3,4-tri-O-benzyl-alpha-D-glucopyranosyl-(1 --> 6))-2,3,4-tri-O-benzyl-1-thio-alpha-D-glucopyranoside) that was constructed from dimer donor iodides in a two-plus-two and a two-plus-four fashion.

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Carbohydrate ConformationGlucosidesGlycosylationIodidesMagnetic Resonance SpectroscopyOligosaccharidesSolutionsStereoisomerismJournal ArticleResearch Support, Non-U.S. Gov'tResearch Support, U.S. Gov't, Non-P.H.S.Research Support, U.S. Gov't, P.H.S.

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Son N Lam, Jacquelyn Gervay-Hague. 2002-11-19. Solution- and solid-phase oligosaccharide synthesis using glucosyl iodides: a comparative study.. https://doi.org/10.1016/s0008-6215(02)00227-6

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