Synthesis of CH2-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct: C -glycosylation

Yu Hidaka; Noriaki Kiya; Makoto Yoritate; Kazuteru Usui; Go Hirai

doi:10.1039/d0cc00785d

Synthesis of CH₂-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct: C -glycosylation

Yu Hidaka, Noriaki Kiya, Makoto Yoritate, Kazuteru Usui, Go Hirai

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

Abstract

We describe a new synthetic approach for C-linked glycolipid analogues, in which the cleavable O-glycosidic linkage is replaced by a carbon unit. Direct C-glycosylation of a conformationally constrained and stable C1-sp³ hybridized xanthate carbohydrate with carefully designed sphingosine units afforded the CH₂-linked analogue of antitumor-active KRN7000 and its glucose congener.

Original language	English
Pages (from-to)	4712-4715
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	34
DOIs	https://doi.org/10.1039/d0cc00785d
Publication status	Published - Apr 30 2020

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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abstract = "We describe a new synthetic approach for C-linked glycolipid analogues, in which the cleavable O-glycosidic linkage is replaced by a carbon unit. Direct C-glycosylation of a conformationally constrained and stable C1-sp3 hybridized xanthate carbohydrate with carefully designed sphingosine units afforded the CH2-linked analogue of antitumor-active KRN7000 and its glucose congener.",

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T2 - C -glycosylation

AU - Hidaka, Yu

AU - Kiya, Noriaki

AU - Yoritate, Makoto

AU - Usui, Kazuteru

AU - Hirai, Go

N1 - Publisher Copyright: This journal is © The Royal Society of Chemistry.

PY - 2020/4/30

Y1 - 2020/4/30

N2 - We describe a new synthetic approach for C-linked glycolipid analogues, in which the cleavable O-glycosidic linkage is replaced by a carbon unit. Direct C-glycosylation of a conformationally constrained and stable C1-sp3 hybridized xanthate carbohydrate with carefully designed sphingosine units afforded the CH2-linked analogue of antitumor-active KRN7000 and its glucose congener.

AB - We describe a new synthetic approach for C-linked glycolipid analogues, in which the cleavable O-glycosidic linkage is replaced by a carbon unit. Direct C-glycosylation of a conformationally constrained and stable C1-sp3 hybridized xanthate carbohydrate with carefully designed sphingosine units afforded the CH2-linked analogue of antitumor-active KRN7000 and its glucose congener.

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JF - Chemical Communications

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Synthesis of CH₂-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct: C -glycosylation

Abstract

All Science Journal Classification (ASJC) codes

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