Conformationally armed glycosyl donors: reactivity quantification, new donors and one pot reactions.
نویسندگان
چکیده
The relative reactivity of conformationally armed thioglycosides is quantified.
منابع مشابه
Chemoselective glycosylations using 2,3-unsaturated-4-keto glycosyl donors.
2,3-Unsaturated-4-keto glycosyl acetates were found to exhibit low reactivity under several glycosylation conditions. Chemoselective glycosylations were effectively performed using 2,3-unsaturated glycosyl and 2,3-dideoxy glycosyl acetates as armed glycosyl donors, and 2,3-unsaturated-4-keto glycosyl acetates as disarmed glycosyl donors.
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O,O-Dimethylthiophosphonosulfenyl bromide (DMTPSB) in combination with silver triflate provides a powerful thiophilic promoter system. Both "armed" and "disarmed" thioglycoside glycosyl donors can be activated to form glycosidic linkages efficiently by the pre-activation protocol. The usefulness of this new promoter is illustrated by a successful iterative one-pot oligosaccharide assembly.
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Well-defined oligosaccharides are important requirements in evaluating structure-activity relationships to decipher the roles of carbohydrates in various physiological processes. These oligosaccharides are accessed mainly through chemical synthesis, which nonetheless remains a huge undertaking despite the many advances in recent years. A combinatorial and regioselective one-pot protection strat...
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عنوان ژورنال:
- Chemical communications
دوره 21 شماره
صفحات -
تاریخ انتشار 2008