3.1 Glycosyl Halides
Kazunobu Toshima
Department of Applied Chemistry, Faculty of Science and Technology,
Keio University, Yokohama 223–8522, Japan
toshima@applc.keio.ac.jp
1
Chemical Glycosylation of Glycosyl Bromide and Chloride . . . . . . . . . . . . . . . . . . . 430
2
Chemical Glycosylation of Glycosyl Iodide . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 433
3
Preparation and Chemical Glycosylation of Glycosyl Fluoride . . . . . . . . . . . . . . . . 433
3.1 Preparation of Glycosyl Fluoride . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 433
3.2 Chemical Glycosylation of Glycosyl Fluoride . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 439
Abstract
This chapter describes the preparations and chemical glycosylation reactions of glycosyl
halides as glycosyl donors including glycosyl bromides, chlorides, iodides, and fluorides.
For a survey on the general current methodological advances, glycosyl halide donors are
classified into four groups based on the type of anomeric functional group and their activating
methods. Among them, glycosyl fluorides, which are frequently and widely used in current
glycosylation reactions, are particularly emphasized and discussed in this chapter.
Keywords
Glycosylation; Glycosyl donor; Glycosyl halide; Glycosyl bromide; Glycosyl chloride; Glycosyl iodide; Glycosyl fluoride
Abbreviations
Ac
acetyl
acac acetylacetone
Ar
aryl
Bn
benzyl
BTF benzotrifluoride
t-Bu tert-butyl
Bz
benzoyl
Cp
cyclopentadienyl
DAST diethylaminosulfur trifluoride
DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
DEAD diethyl azodicarboxylate
DIEA N,N-diisopropylethylamine
In: Glycoscience. Fraser-Reid B, Tatsuta K, Thiem J (eds)
Chapter-DOI 10-1007/978-3-540-30429-6_10: © Springer-Verlag Berlin Heidelberg 2008