Conformationally armed 3,6-tethered glycosyl donors: synthesis, conformation, reactivity, and selectivity.
作者： Mads Heuckendorff , Christian Marcus Pedersen , Mikael Bols
DOI: 10.1021/JO4012464
关键词: Anomer 、 Selectivity 、 Carbohydrate conformation 、 Reactivity (chemistry) 、 Fluoride 、 Glycosyl 、 Stereochemistry 、 Steric effects 、 Glycosylation 、 Chemistry
摘要: The reactivity and selectivity of 3,6-tethered glycosyl donors have been studied using acceptors with different steric electronic characteristics. Eight (four anomeric pairs) 3,6-bridged-glycosyl were synthesized in high yields from their common parent sugars. glycosylation properties tested at least three several promoter systems. Thiophenyl 2,4-di-O-benzyl-3,6-O-(di-tert-butylsilylene)-α-d-glucopyranoside gave α/β mixtures standard NIS/TfOH mediated activation, whereas the corresponding fluoride was found to be highly β-selective, when SnCl2/AgB(C6F5)4 as system. Mannosyl α-selective despite altered conformation. Galactosylations generally α-selective, but more β-selective galactosyl depending on acceptor used. 2-azido-2-deoxy-4-O-benzyl-3,6-O-(di-tert-butylsilylene)-α-d-glucopyranoside . in...
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