Efficient C-arylglycosylation of 1-O-methyl sugar by novel use of TMSOTf-AgClO4 catalyst system

Kazunobu Toshima; Goh Matsuo; Kuniaki Tatsuta

doi:10.1016/0040-4039(92)88170-A

Efficient C-arylglycosylation of 1-O-methyl sugar by novel use of TMSOTf-AgClO₄ catalyst system

Kazunobu Toshima, Goh Matsuo, Kuniaki Tatsuta

Department of Applied Chemistry

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

32 Citations (Scopus)

Abstract

Highly β-stereoselective C-arylglycosylations of the 1-O-methyl sugars 1∼4 with 2-naphthol (9) were effectively achieved by novel combinational use of a catalytic amount of TMSOTf-AgClO₄ as an activator. Also, C-arylglycosylations of the 1-O-acetyl sugars 5∼8 with 9 in this way worked as well.

Original language	English
Pages (from-to)	2175-2178
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	16
DOIs	https://doi.org/10.1016/0040-4039(92)88170-A
Publication status	Published - 1992 Apr 14

Keywords

1-O-methyl sugar
2-naphthol
TMSOTf-AgClO
catalyst system
β-stereoselective C-arylglycosylation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/0040-4039(92)88170-A

Cite this

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title = "Efficient C-arylglycosylation of 1-O-methyl sugar by novel use of TMSOTf-AgClO4 catalyst system",

abstract = "Highly β-stereoselective C-arylglycosylations of the 1-O-methyl sugars 1∼4 with 2-naphthol (9) were effectively achieved by novel combinational use of a catalytic amount of TMSOTf-AgClO4 as an activator. Also, C-arylglycosylations of the 1-O-acetyl sugars 5∼8 with 9 in this way worked as well.",

keywords = "1-O-methyl sugar, 2-naphthol, TMSOTf-AgClO, catalyst system, β-stereoselective C-arylglycosylation",

author = "Kazunobu Toshima and Goh Matsuo and Kuniaki Tatsuta",

note = "Funding Information: We areg ratefutl o theI nstituteo f Microbial Chemistryfo r theg eneroussu pporot f our programF. inancial supportsb y the Ministry of Education,S ciencea nd Culture( Grant-in-Aid Scientific Researchi)s gratefully acknowledged.",

year = "1992",

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doi = "10.1016/0040-4039(92)88170-A",

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T1 - Efficient C-arylglycosylation of 1-O-methyl sugar by novel use of TMSOTf-AgClO4 catalyst system

AU - Toshima, Kazunobu

AU - Matsuo, Goh

AU - Tatsuta, Kuniaki

N1 - Funding Information: We areg ratefutl o theI nstituteo f Microbial Chemistryfo r theg eneroussu pporot f our programF. inancial supportsb y the Ministry of Education,S ciencea nd Culture( Grant-in-Aid Scientific Researchi)s gratefully acknowledged.

PY - 1992/4/14

Y1 - 1992/4/14

N2 - Highly β-stereoselective C-arylglycosylations of the 1-O-methyl sugars 1∼4 with 2-naphthol (9) were effectively achieved by novel combinational use of a catalytic amount of TMSOTf-AgClO4 as an activator. Also, C-arylglycosylations of the 1-O-acetyl sugars 5∼8 with 9 in this way worked as well.

AB - Highly β-stereoselective C-arylglycosylations of the 1-O-methyl sugars 1∼4 with 2-naphthol (9) were effectively achieved by novel combinational use of a catalytic amount of TMSOTf-AgClO4 as an activator. Also, C-arylglycosylations of the 1-O-acetyl sugars 5∼8 with 9 in this way worked as well.

KW - 1-O-methyl sugar

KW - 2-naphthol

KW - TMSOTf-AgClO

KW - catalyst system

KW - β-stereoselective C-arylglycosylation

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