Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides

Tomoya Kimura; Daisuke Takahashi; Kazunobu Toshima

doi:10.1021/acs.joc.5b01542

Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides

Tomoya Kimura, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Article

11 Citations (Scopus)

Abstract

The glycosylations of glycals and alcohols using N-iodosuccinimide (NIS) and a catalytic amount of PPh₃ effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodoglycosylations with PPh₃ significantly increased in comparison to that using NIS alone as an activator. In addition, the glycosylations of glycals and alcohols using catalytic amounts of NIS and P(OPh)₃ were effectively realized to give the corresponding 2-deoxyglycosides in high yields.

Original language	English
Pages (from-to)	9552-9562
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	80
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.5b01542
Publication status	Published - 2015 Oct 2

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Phosphorus Compounds

Glycosylation

Alcohols

N-iodosuccinimide

ASJC Scopus subject areas

Organic Chemistry

Cite this

Kimura, T., Takahashi, D., & Toshima, K. (2015). Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides. Journal of Organic Chemistry, 80(19), 9552-9562. https://doi.org/10.1021/acs.joc.5b01542

Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides. / Kimura, Tomoya; Takahashi, Daisuke ; Toshima, Kazunobu.

In: Journal of Organic Chemistry, Vol. 80, No. 19, 02.10.2015, p. 9552-9562.

Research output: Contribution to journal › Article

Kimura, T, Takahashi, D & Toshima, K 2015, 'Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides', Journal of Organic Chemistry, vol. 80, no. 19, pp. 9552-9562. https://doi.org/10.1021/acs.joc.5b01542

Kimura T, Takahashi D , Toshima K. Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides. Journal of Organic Chemistry. 2015 Oct 2;80(19):9552-9562. https://doi.org/10.1021/acs.joc.5b01542

Kimura, Tomoya ; Takahashi, Daisuke ; Toshima, Kazunobu. / Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 19. pp. 9552-9562.

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10.1021/acs.joc.5b01542