Glycosyl fluorides in glycosidations

Kazunobu Toshima

doi:10.1016/S0008-6215(99)00325-0

Glycosyl fluorides in glycosidations

Kazunobu Toshima

応用化学科

研究成果: Review article › 査読

113 被引用数 (Scopus)

抄録

This short review deals with the recent progress in chemical O- glycosidation and C-glycosylation methods using glycosyl fluorides as glycosyl donors. Pyranosyl and furanosyl fluorides were effectively activated by fluorophilic reagents such as SnCl₂-AgClO₄, SnCl₂-TrClO₄, SnCl₂- AgOTf, TMSOTf, SiF₄, BF₃·Et₂O, TiF₄, SnF₄, Cp₂MCl₂-AgClO₄ (M = Zr or Hf), Cp₂ZrCl₂-AgBF₄, Cp₂HfCl₂-AgOTf, Bu₂Sn(ClO₄)₂, Me₂GaCl, Tf₂O, LiClO₄, Yb(OTf)₃, La(ClO₄)₃·nH₂O, La(ClO₄)₃·nH₂O-Sn(OTf)₂, Yb- Amberlyst 15, SO₄/ZrO₂, Nafion-H®, montmorillonite K-10, and TrB(C₆F₅)₄ to react with alcohols to give the corresponding O-glycosides in high yields. Furthermore, several types of C-glycosides, such as aryl, allyl and alkyl C- glycosyl derivatives, were also obtained by the glycosylation using glycosyl fluorides and the corresponding nucleophile with or without a Lewis acid. (C) 2000 Elsevier Science Ltd.

本文言語	English
ページ（範囲）	15-26
ページ数	12
ジャーナル	Carbohydrate Research
巻	327
号	1-2
DOI	https://doi.org/10.1016/S0008-6215(99)00325-0
出版ステータス	Published - 2000 7 10

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

文献へのアクセス

10.1016/S0008-6215(99)00325-0

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引用スタイル

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abstract = "This short review deals with the recent progress in chemical O- glycosidation and C-glycosylation methods using glycosyl fluorides as glycosyl donors. Pyranosyl and furanosyl fluorides were effectively activated by fluorophilic reagents such as SnCl2-AgClO4, SnCl2-TrClO4, SnCl2- AgOTf, TMSOTf, SiF4, BF3·Et2O, TiF4, SnF4, Cp2MCl2-AgClO4 (M = Zr or Hf), Cp2ZrCl2-AgBF4, Cp2HfCl2-AgOTf, Bu2Sn(ClO4)2, Me2GaCl, Tf2O, LiClO4, Yb(OTf)3, La(ClO4)3·nH2O, La(ClO4)3·nH2O-Sn(OTf)2, Yb- Amberlyst 15, SO4/ZrO2, Nafion-H{\textregistered}, montmorillonite K-10, and TrB(C6F5)4 to react with alcohols to give the corresponding O-glycosides in high yields. Furthermore, several types of C-glycosides, such as aryl, allyl and alkyl C- glycosyl derivatives, were also obtained by the glycosylation using glycosyl fluorides and the corresponding nucleophile with or without a Lewis acid. (C) 2000 Elsevier Science Ltd.",

keywords = "C- Glycoside, C-Glycosidation, Glycosyl fluoride, O-Glycosidation, O-Glycoside",

author = "Kazunobu Toshima",

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N2 - This short review deals with the recent progress in chemical O- glycosidation and C-glycosylation methods using glycosyl fluorides as glycosyl donors. Pyranosyl and furanosyl fluorides were effectively activated by fluorophilic reagents such as SnCl2-AgClO4, SnCl2-TrClO4, SnCl2- AgOTf, TMSOTf, SiF4, BF3·Et2O, TiF4, SnF4, Cp2MCl2-AgClO4 (M = Zr or Hf), Cp2ZrCl2-AgBF4, Cp2HfCl2-AgOTf, Bu2Sn(ClO4)2, Me2GaCl, Tf2O, LiClO4, Yb(OTf)3, La(ClO4)3·nH2O, La(ClO4)3·nH2O-Sn(OTf)2, Yb- Amberlyst 15, SO4/ZrO2, Nafion-H®, montmorillonite K-10, and TrB(C6F5)4 to react with alcohols to give the corresponding O-glycosides in high yields. Furthermore, several types of C-glycosides, such as aryl, allyl and alkyl C- glycosyl derivatives, were also obtained by the glycosylation using glycosyl fluorides and the corresponding nucleophile with or without a Lewis acid. (C) 2000 Elsevier Science Ltd.

AB - This short review deals with the recent progress in chemical O- glycosidation and C-glycosylation methods using glycosyl fluorides as glycosyl donors. Pyranosyl and furanosyl fluorides were effectively activated by fluorophilic reagents such as SnCl2-AgClO4, SnCl2-TrClO4, SnCl2- AgOTf, TMSOTf, SiF4, BF3·Et2O, TiF4, SnF4, Cp2MCl2-AgClO4 (M = Zr or Hf), Cp2ZrCl2-AgBF4, Cp2HfCl2-AgOTf, Bu2Sn(ClO4)2, Me2GaCl, Tf2O, LiClO4, Yb(OTf)3, La(ClO4)3·nH2O, La(ClO4)3·nH2O-Sn(OTf)2, Yb- Amberlyst 15, SO4/ZrO2, Nafion-H®, montmorillonite K-10, and TrB(C6F5)4 to react with alcohols to give the corresponding O-glycosides in high yields. Furthermore, several types of C-glycosides, such as aryl, allyl and alkyl C- glycosyl derivatives, were also obtained by the glycosylation using glycosyl fluorides and the corresponding nucleophile with or without a Lewis acid. (C) 2000 Elsevier Science Ltd.

KW - C- Glycoside

KW - C-Glycosidation

KW - Glycosyl fluoride

KW - O-Glycosidation

KW - O-Glycoside

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