DISAL glycosyl donors for efficient glycosylations under acidic conditions: Application to solid-phase oligosaccharide synthesis

Lars Petersen; Knud J. Jensen

doi:10.1039/B105872J

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DISAL glycosyl donors for efficient glycosylations under acidic conditions: Application to solid-phase oligosaccharide synthesis^1,2

Lars Petersen^a and Knud J. Jensen*^a

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* Corresponding authors

^a Department of Chemistry, Building 201, Kemitorvet, Technical University of Denmark, Denmark
E-mail: kj@kemi.dtu.dk
Fax: (+45) 45 93 39 68
Tel: (+45) 45252141

Abstract

The use of DISAL (methyl dinitrosalicylate) glycosyl donors in efficient Lewis acid-promoted glycosylations is reported. N-Acetyl-D-glucosamine monosaccharide acceptors are successfully glycosylated at O-6 or O-4 using benzyl- and benzoyl-protected DISAL donors in CH₂Cl₂ or nitromethane in the presence of LiClO₄. The resultant disaccharides are isolated in yields ranging from 35 to 93%. Other Lewis acids such as FeCl₃, TMSOTf, or BF₃·Et₂O also prove efficient for glycosylation of the secondary alcohol cyclohexanol. However, for the synthesis of disaccharides, the mild activation by LiClO₄ gives higher yields. This approach is extended to efficient solid-phase glycosylation of a D-glucosamine derivative anchored by the 2-amino group through a Backbone Amide Linker (BAL) to a polystyrene support.

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Article information

DOI: https://doi.org/10.1039/B105872J
Article type: Paper
Submitted: 03 Jul 2001
Accepted: 27 Jul 2001
First published: 03 Sep 2001

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J. Chem. Soc., Perkin Trans. 1, 2001, 2175-2182

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DISAL glycosyl donors for efficient glycosylations under acidic conditions: Application to solid-phase oligosaccharide synthesis

L. Petersen and K. J. Jensen, J. Chem. Soc., Perkin Trans. 1, 2001, 2175 DOI: 10.1039/B105872J

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Journal of the Chemical Society, Perkin Transactions 1