Regioselective One-pot Protection and Protection-glycosylation of Carbohydrates

Authors

  • Cheng-Chung Wang Institute of Chemistry Sinica 128, Section 2, Academia Road 115 Taipei, Taiwan;, Email: wangcc@chem.sinica.edu.tw
  • Medel Manuel L. Zulueta Genomics Research Center Academia Sinica 128, Section 2, Academia Road 115 Taipei, Taiwan
  • shang-Cheng Hung Institute of Chemistry Sinica 128, Section 2, Academia Road 115 Taipei, Taiwan;, Email: schung@gate.sinica.edu.tw

DOI:

https://doi.org/10.2533/chimia.2011.54

Keywords:

Carbohydrate chemistry, Glycosylation, One-pot reactions, Protective groups, Regioselective etherification

Abstract

Deciphering the roles and structure–activity relationships of carbohydrates in biological processes requires access to sugar molecules of confirmed structure and high purity. Chemical synthesis is one of the best ways to obtain such access. However, the synthesis of carbohydrates has long been impeded by two major challenges – the regioselective protection of the polyol moiety of each monosaccharide building block and the stereoselective glycosylation to produce oligosaccharides of desired length. Here, we review the development of the first regioselective protection-glycosylation and a revolutionary regioselective combinatorial one-pot protection of monosaccharides that can be used to differentiate the various hydroxy groups of monosaccharides with a vast array of orthogonal protective groups in one-pot procedures.

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Published

2011-02-23

Issue

Section

Scientific Articles

How to Cite

[1]
C.-C. Wang, M. M. L. Zulueta, shang-C. Hung, Chimia 2011, 65, 54, DOI: 10.2533/chimia.2011.54.