STEREODIRECTING EFFECT OF CYCLIC SILYL PROTECTING GROUPS IN CHEMICAL GLYCOSYLATION

Author:

Yagami Nahoko,Imamura Akihiro1

Affiliation:

1. Department of Applied Bio-organic Chemistry, Faculty of Applied Biological Sciences, Gifu University

Publisher

United Graduate School of Agricultural Science

Subject

General Agricultural and Biological Sciences

Reference46 articles.

1. Boltje TJ, Zhong W, Park J, Wolfert MA, Chen W and Boons GJ (2012) Chemical synthesis and immunological evaluation of the inner core oligosaccharide of Francisella tularensis. J. Am. Chem. Soc., 134: 14255-14262.

2. Crich D and Dudkin V (2001) Why are the hydroxy groups of partially protected N-acetylglucosamine derivatives such poor glycosyl acceptors, and what can be done about it? A comparative study of the reactivity of N-acetyl-, N-phthalimido-, and 2-azido-2-deoxy-glucosamine derivatives in glycosylation. 2-Picolinyl ethers as reactivity-enhancing replacements for benzyl ethers. J. Am. Chem. Soc., 123: 6819-6825.

3. Crich D, Pedersen CM, Bowers AA and Wink DJ (2007) On the use of 3,5-O-benzylidene and 3,5-O-(di-tert-butylsilylene)-2-O-benzylarabinothiofuranosides and their sulfoxides as glycosyl donors for the synthesis of β-arabinofuranosides: Importance of the activation method. J. Org. Chem., 72: 1553-1565.

4. Crich D and Sun S (1996) Formation of β-mannopyranosides of primary alcohols using the sulfoxide method. J. Org. Chem., 61: 4506-4507.

5. Crich D and Sun S (1998) Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflates. Tetrahedron, 54: 8321-8348.

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