NaHSO4 supported on silica gel: an alternative catalyst for Ferrier rearrangement of glycals

Kinfe, Henok H.; Mebrahtu, Fanuel M.; Sithole, Khuphukile

doi:10.1016/j.carres.2011.08.023

Cited by 22 publications

(12 citation statements)

References 42 publications

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“…Montmorillonite K‐10 clay‐supported Bi(OTf) 3 has also been illustrated to achieve the synthesis of various types of sialic acid through Ferrier transformation. Other versatile catalyst systems, for example HClO 4 –silica, CF 3 SO 3 H–silica, NaHSO 4 –silica, and H 2 SO 4 —silica, have been used for the synthesis of a wide range of pseudoglycosides. In the context of organic acid catalysts, when acetic acid failed to yield any desired unsaturated glycoside, Liu and co‐workers decided to test the effectiveness of camphorsulfonic acid (CSA) as a probable catalyst for triggering the formation of pseudoglycosides.…”

Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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The development of glycobiology relies on the sources of particular oligosaccharides in their purest forms. As the isolation of the oligosaccharide structures from natural sources is not a reliable option for providing samples with homogeneity, chemical means become pertinent. The growing demand for diverse oligosaccharide structures has prompted the advancement of chemical strategies to stitch sugar molecules with precise stereo‐ and regioselectivity through the formation of glycosidic bonds. This Review will focus on the key developments towards chemical O‐glycosylations in the current century. Synthesis of novel glycosyl donors and acceptors and their unique activation for successful glycosylation are discussed. This Review concludes with a summary of recent developments and comments on future prospects.

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Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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“…In this context, different research groups have reported catalysts based on protic acids adsorbed on silica gel. These acids include HClO 4 ,101,102 H 2 SO 4 ,103,104 HBF 4 ,105 phosphomolybdic acid (PMA),106 CF 3 SO 3 H,107 and NaHSO 4 108. In these transformations a variety of oxygen nucleophiles such as alcohols, phenols, or monosaccharides were used as glycosyl acceptors.…”

Section: Promoters For the Rearrangement Of Glycalsmentioning

confidence: 99%

Recent Developments in the Ferrier Rearrangement

et al. 2013

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Glycals (1,2‐unsaturated, cyclic carbohydrate derivatives) readily undergo (catalyzed) substitution reactions at C‐1 accompanied by allylic rearrangement. This reaction, currently named Ferrier rearrangement, or the Ferrier I reaction, has established itself as a useful synthetic tool for carbohydrate transformations. By means of this reaction, glycals can be converted into highly useful 2,3‐unsaturated glycosides. This review summarizes recent developments in the use of promoters for the Ferrier rearrangement of O‐, N‐, C‐ and S‐nucleophiles with glycals.

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“…For applications of pseudoglycals, see: Domon et al (2005); Danishefsky & Bilodeau (1996); Griffith & Danishefsky (1991); Halcomb et al (1995); Bracherro et al (1998); Dorgan & Jackson (1996); Chambers et al (2005); Minuth & Boysen (2009). For background to the synthetic methodology of glycosides, see: Kinfe et al (2011). For the preparation of the acid catalyst NaHSO 4 -SiO 2 , see: Breton (1997).…”

Section: Related Literaturementioning

confidence: 99%