An imrpoved practical method for synthesis of aryl C-glycosides from unprotected methyl glycosides and 1-hydroxy sugars

Kazunobu Toshima; Goh Matsuo; Masaya Nakata

doi:10.1039/C39940000997

An imrpoved practical method for synthesis of aryl C-glycosides from unprotected methyl glycosides and 1-hydroxy sugars

Kazunobu Toshima, Goh Matsuo, Masaya Nakata

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研究成果: Article › 査読

31 被引用数 (Scopus)

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Aryl C-glycosidations of the unprotected methyl glycosides 9-12 and the unprotected 1-hydroxy sugars 14 and 15 with 2-naphthol 6 using TMSOTf proceed much more effectively than those of the acylated methyl glycosides 4 and 5; the unprotected methyl glycoside 10 is also smoothly coupled with other phenol and naphthol derivatives 25-27 to give the corresponding unprotected o-hydroxyaryl β-C-glycosides in high yields (TMSOTf = trimethylsilyloxytrifluoromethanesulfonate).

本文言語	English
ページ（範囲）	997-998
ページ数	2
ジャーナル	Journal of the Chemical Society, Chemical Communications
号	8
DOI	https://doi.org/10.1039/C39940000997
出版ステータス	Published - 1994 12月 1

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N2 - Aryl C-glycosidations of the unprotected methyl glycosides 9-12 and the unprotected 1-hydroxy sugars 14 and 15 with 2-naphthol 6 using TMSOTf proceed much more effectively than those of the acylated methyl glycosides 4 and 5; the unprotected methyl glycoside 10 is also smoothly coupled with other phenol and naphthol derivatives 25-27 to give the corresponding unprotected o-hydroxyaryl β-C-glycosides in high yields (TMSOTf = trimethylsilyloxytrifluoromethanesulfonate).

AB - Aryl C-glycosidations of the unprotected methyl glycosides 9-12 and the unprotected 1-hydroxy sugars 14 and 15 with 2-naphthol 6 using TMSOTf proceed much more effectively than those of the acylated methyl glycosides 4 and 5; the unprotected methyl glycoside 10 is also smoothly coupled with other phenol and naphthol derivatives 25-27 to give the corresponding unprotected o-hydroxyaryl β-C-glycosides in high yields (TMSOTf = trimethylsilyloxytrifluoromethanesulfonate).

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An imrpoved practical method for synthesis of aryl C-glycosides from unprotected methyl glycosides and 1-hydroxy sugars

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