Novel stereocontrolled glycosidations using a solid acid, SO4/ZrO2, for direct syntheses of α- and β-mannopyranosides

Kazunobu Toshima, Ken Ichi Kasumi, Shuichi Matsumura

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Abstract

Novel stereocontrolled glycosidations using an environmentally friendly solid acid, sulfated zirconia (SO4/ZrO2), for direct syntheses of α- and β-mannopyranosides have been developed. The glycosidations of the totally benzylated mannopyranosyl fluoride 1 and various alcohols using SO4/ZrO2 in CH3CN at 40°C for 15 h exclusively gave the corresponding α-mannopyranosides. On the other hand, the corresponding β-mannopyranosides were selectively obtained by the glycosidations of 1 and various alcohols employing SO4/ZrO2 in the presence of molecular sieves 5Å in Et2O at 25°C for 15 h.

Original languageEnglish
Pages (from-to)643-645
Number of pages3
JournalSynlett
Issue number6
Publication statusPublished - 1998 Jun

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Mannose
Acids
Alcohols
Molecular sieves
Fluorides

ASJC Scopus subject areas

  • Organic Chemistry

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Novel stereocontrolled glycosidations using a solid acid, SO4/ZrO2, for direct syntheses of α- and β-mannopyranosides. / Toshima, Kazunobu; Kasumi, Ken Ichi; Matsumura, Shuichi.

In: Synlett, No. 6, 06.1998, p. 643-645.

Research output: Contribution to journalArticle

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abstract = "Novel stereocontrolled glycosidations using an environmentally friendly solid acid, sulfated zirconia (SO4/ZrO2), for direct syntheses of α- and β-mannopyranosides have been developed. The glycosidations of the totally benzylated mannopyranosyl fluoride 1 and various alcohols using SO4/ZrO2 in CH3CN at 40°C for 15 h exclusively gave the corresponding α-mannopyranosides. On the other hand, the corresponding β-mannopyranosides were selectively obtained by the glycosidations of 1 and various alcohols employing SO4/ZrO2 in the presence of molecular sieves 5{\AA} in Et2O at 25°C for 15 h.",
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