Glycosyl fluorides in glycosidations

Kazunobu Toshima

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

Glycosyl fluorides in glycosidations

Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Review article › peer-review

128 Citations (Scopus)

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®, 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.

Original language	English
Pages (from-to)	15-26
Number of pages	12
Journal	Carbohydrate Research
Volume	327
Issue number	1-2
DOIs	https://doi.org/10.1016/S0008-6215(99)00325-0
Publication status	Published - 2000 Jul 10

Keywords

C- Glycoside
C-Glycosidation
Glycosyl fluoride
O-Glycosidation
O-Glycoside

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/S0008-6215(99)00325-0

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title = "Glycosyl fluorides in glycosidations",

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",

year = "2000",

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doi = "10.1016/S0008-6215(99)00325-0",

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AU - Toshima, Kazunobu

PY - 2000/7/10

Y1 - 2000/7/10

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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ER -

Glycosyl fluorides in glycosidations

Abstract

Keywords

ASJC Scopus subject areas

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