Glycosyl 2-pyridinecarboxylate as an effective glycosyl donor: Glycosidation of mannose, 2-azidosugar, and 2-deoxysugar into disaccharides

Hironori Furukawa; Kazunori Koide; Ken Ichi Takao; Susumu Kobayashi

doi:10.1248/cpb.46.1244

Glycosyl 2-pyridinecarboxylate as an effective glycosyl donor: Glycosidation of mannose, 2-azidosugar, and 2-deoxysugar into disaccharides

Hironori Furukawa, Kazunori Koide, Ken Ichi Takao, Susumu Kobayashi

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

16 Citations (Scopus)

Abstract

Glycosylation reactions using a glycosyl 2-pyridinecarboxylate as a glycosyl donor were performed. Glycosyl 2-pyridinecarboxylate was designed based on a variation of the Remote Activation Concept and is activated through bidentate coordination to mild Lewis acids such as copper triflate and tin triflate. This method was effective for the glycosidation of not only glucose, but several other sugars such as the mannose-type, 2-azidosugar- type, and 2-deoxysugar-type. Various disaccharides were obtained in excellent yield by this reaction.

Original language	English
Pages (from-to)	1244-1247
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	46
Issue number	8
DOIs	https://doi.org/10.1248/cpb.46.1244
Publication status	Published - 1998 Jan 1
Externally published	Yes

Keywords

Copper triflate
Disaccharide
Glycosyl 2-pyridinecarboxylate
Glycosyl donor
Glycosylation
Tin triflate

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.46.1244

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abstract = "Glycosylation reactions using a glycosyl 2-pyridinecarboxylate as a glycosyl donor were performed. Glycosyl 2-pyridinecarboxylate was designed based on a variation of the Remote Activation Concept and is activated through bidentate coordination to mild Lewis acids such as copper triflate and tin triflate. This method was effective for the glycosidation of not only glucose, but several other sugars such as the mannose-type, 2-azidosugar- type, and 2-deoxysugar-type. Various disaccharides were obtained in excellent yield by this reaction.",

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T1 - Glycosyl 2-pyridinecarboxylate as an effective glycosyl donor

T2 - Glycosidation of mannose, 2-azidosugar, and 2-deoxysugar into disaccharides

AU - Furukawa, Hironori

AU - Koide, Kazunori

AU - Takao, Ken Ichi

AU - Kobayashi, Susumu

PY - 1998/1/1

Y1 - 1998/1/1

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AB - Glycosylation reactions using a glycosyl 2-pyridinecarboxylate as a glycosyl donor were performed. Glycosyl 2-pyridinecarboxylate was designed based on a variation of the Remote Activation Concept and is activated through bidentate coordination to mild Lewis acids such as copper triflate and tin triflate. This method was effective for the glycosidation of not only glucose, but several other sugars such as the mannose-type, 2-azidosugar- type, and 2-deoxysugar-type. Various disaccharides were obtained in excellent yield by this reaction.

KW - Copper triflate

KW - Disaccharide

KW - Glycosyl 2-pyridinecarboxylate

KW - Glycosyl donor

KW - Glycosylation

KW - Tin triflate

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Glycosyl 2-pyridinecarboxylate as an effective glycosyl donor: Glycosidation of mannose, 2-azidosugar, and 2-deoxysugar into disaccharides

Abstract

Keywords

ASJC Scopus subject areas

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