Catalytic stereospecific O-glycosylation

Kowalska, Karolina; Pedersen, Christian

doi:10.1039/c6cc10076g

Cited by 25 publications

(24 citation statements)

References 48 publications

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“…The glycosylation reactions of glucosyl donor 16 with a variety of glycosyl acceptors were conducted in a fashion similar to that mentioned earlier. Glycosidation of donor 16 with 1-adamantanol acceptor 18 to form glycoside 30 45 was enhanced from 61% (30 min, no HOFox) to 90% (30 min, 25 mol % HOFox, entry 7, Table 3). The stereoselectivity of both reactions was the same, α / β = 10/1.…”

Section: Resultsmentioning

confidence: 99%

Regenerative Glycosylation

et al. 2017

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Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.

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Section: Resultsmentioning

confidence: 99%

Regenerative Glycosylation

et al. 2017

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“…79 Reactions employing the more nucleophilic triflate progress via the formation of a glycosyl triflate. 78 …”

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confidence: 99%

Trifluoromethanesulfonate Anion as Nucleophile in Organic Chemistry

2017

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Although the triflate ion is not generally perceived as a nucleophile many examples of its behavior as such exist in the literature. This synopsis presents an overview of such reactions, in which triflate may be either a stoichiometric or catalytic nucleophile, leading to the suggestion that nucleophilic catalysis by triflate may be more common than generally accepted, albeit hidden by the typical reactivity of organic triflates which complicates their observation as intermediates.

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“…Notably, little selectivity was observed with OTf- (Table 1, entry 5), which is in accordance with the previously reported counterion effect of OTf - . [40, 41]…”

Section: Resultsmentioning

confidence: 99%