Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides

Kazunobu Toshima; Hideyuki Nagai; Ken Ichi Kasumi; Kanako Kawahara; Shuichi Matsumura

doi:10.1016/j.tet.2004.04.071

Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides

Kazunobu Toshima, Hideyuki Nagai, Ken Ichi Kasumi, Kanako Kawahara, Shuichi Matsumura

Department of Applied Chemistry

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

45 Citations (Scopus)

Abstract

Novel α- and β-stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia (SO₄/ZrO₂), as an activator have been developed. The glycosidations of manno- and 2-deoxyglucopyranosyl α-fluorides with several alcohols using SO ₄/ZrO₂ in MeCN proceeded α-stereoselectively, while those with the same activator in the presence of MS 5A in Et₂O occurred with β-stereoselectivity. Thus, both the α- and β-manno- and 2-deoxyglucopyranosides were effectively obtained by the present glycosidations.

Original language	English
Pages (from-to)	5331-5339
Number of pages	9
Journal	Tetrahedron
Volume	60
Issue number	25
DOIs	https://doi.org/10.1016/j.tet.2004.04.071
Publication status	Published - 2004 Jun 14

Keywords

2-Deoxypyranoside
Glycosidation
Heterogeneous solid acid
Mannopyranoside
Sulfated zirconia

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2004.04.071

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title = "Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides",

abstract = "Novel α- and β-stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia (SO4/ZrO2), as an activator have been developed. The glycosidations of manno- and 2-deoxyglucopyranosyl α-fluorides with several alcohols using SO 4/ZrO2 in MeCN proceeded α-stereoselectively, while those with the same activator in the presence of MS 5A in Et2O occurred with β-stereoselectivity. Thus, both the α- and β-manno- and 2-deoxyglucopyranosides were effectively obtained by the present glycosidations.",

keywords = "2-Deoxypyranoside, Glycosidation, Heterogeneous solid acid, Mannopyranoside, Sulfated zirconia",

author = "Kazunobu Toshima and Hideyuki Nagai and Kasumi, {Ken Ichi} and Kanako Kawahara and Shuichi Matsumura",

note = "Funding Information: This research was partially supported by Grant-in-Aid for the 21st Century COE program {\textquoteleft}KEIO Life Conjugate Chemistry{\textquoteright} from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.",

year = "2004",

month = jun,

day = "14",

doi = "10.1016/j.tet.2004.04.071",

language = "English",

volume = "60",

pages = "5331--5339",

journal = "Tetrahedron",

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T1 - Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides

AU - Toshima, Kazunobu

AU - Nagai, Hideyuki

AU - Kasumi, Ken Ichi

AU - Kawahara, Kanako

AU - Matsumura, Shuichi

N1 - Funding Information: This research was partially supported by Grant-in-Aid for the 21st Century COE program ‘KEIO Life Conjugate Chemistry’ from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

PY - 2004/6/14

Y1 - 2004/6/14

N2 - Novel α- and β-stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia (SO4/ZrO2), as an activator have been developed. The glycosidations of manno- and 2-deoxyglucopyranosyl α-fluorides with several alcohols using SO 4/ZrO2 in MeCN proceeded α-stereoselectively, while those with the same activator in the presence of MS 5A in Et2O occurred with β-stereoselectivity. Thus, both the α- and β-manno- and 2-deoxyglucopyranosides were effectively obtained by the present glycosidations.

AB - Novel α- and β-stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia (SO4/ZrO2), as an activator have been developed. The glycosidations of manno- and 2-deoxyglucopyranosyl α-fluorides with several alcohols using SO 4/ZrO2 in MeCN proceeded α-stereoselectively, while those with the same activator in the presence of MS 5A in Et2O occurred with β-stereoselectivity. Thus, both the α- and β-manno- and 2-deoxyglucopyranosides were effectively obtained by the present glycosidations.

KW - 2-Deoxypyranoside

KW - Glycosidation

KW - Heterogeneous solid acid

KW - Mannopyranoside

KW - Sulfated zirconia

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DO - 10.1016/j.tet.2004.04.071

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JO - Tetrahedron

JF - Tetrahedron

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ER -

Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides

Abstract

Keywords

ASJC Scopus subject areas

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