Volume 32, Issue 45
Natural Products
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ChemInform Abstract: New Design Concepts for Constraining Glycosylated Amino Acids.

Jonathan W. Lane

Jonathan W. Lane

Dep. Chem. Biochem., Univ. Colo., Boulder, CO 80309, USA

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Randall L. Halcomb

Randall L. Halcomb

Dep. Chem. Biochem., Univ. Colo., Boulder, CO 80309, USA

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First published: 23 May 2010

Abstract

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ChemInform Abstract

Glycopeptides (VI) and (VII), representing the D- and L-serine configuration, are prepared through a convergent strategy involving the nucleophilic addition of alkyne (II) to the lactone (III) followed by deprotection to afford diol (IV). A one-pot partial reduction/spiroketalization reaction of diol (V) gives a product mixture containing at least two epimeric spiro compounds (V). Further transformations of this mixture afford the desired separable glycopeptides.

chemical structure image

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