Journal
CARBOHYDRATE RESEARCH
Volume 396, Issue -, Pages 25-36Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2014.05.017
Keywords
Arabinofuranose; Benzyl-free approach; 1,2-cis-Stereoselectivity; O-Trifluoroacetyl group; Electron-withdrawing protecting groups
Funding
- Russian Foundation for Basic Research [11-03-00918, 13-03-00666]
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The influence of O-trifluoroacetyl (TFA) groups at different positions of thioglycoside glycosyl donors on stereoselectivity of alpha-arabinofuranosylation leading to corresponding disaccharides was studied. It was shown that TFA group in thioglycoside glycosyl donors, when combined with 2-O-(triisopropylsilyl) (TIPS) non-participating group, may be regarded as an electron-withdrawing protecting group that may enhance 1,2-cis-selectivity in arabinofuranosylation, the results strongly depending on the nature of glycosyl acceptor. The reactivities of the glycosyl donors were compared with those of a similar thioglycoside with O-pentafluoropropionyl groups and the known phenyl 3,5-O-(di-tert-butylsilylene)-1-thio-alpha-D-arabinofuranosides with 2-O-TIPS and 2-O-benzyl groups. The 'matching' in the donor-acceptor combination was found to be critical for achieving both high reactivity of glycosyl donor and beta-stereoselectivity of arabinofuranosylation. The use of glycosyl donors with TFA and silyl protection may be useful in the realization of the benzyl-free approach to oligoarabinofuranosides with azido group in aglycon-convenient building blocks for the preparation of neoglycoconjugates. (C) 2014 Elsevier Ltd. All rights reserved.
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