An efficient glycosidation method using 2,3-unsaturated glycosyl donors

Kaname Sasaki; Shuichi Matsumura; Kazunobu Toshima

doi:10.1016/j.tetlet.2006.10.095

An efficient glycosidation method using 2,3-unsaturated glycosyl donors

Kaname Sasaki, Shuichi Matsumura, Kazunobu Toshima

Department of Applied Chemistry

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

14 Citations (Scopus)

Abstract

A novel class of 'armed' glycosyl donors containing a double bond at the C-2 position was designed by mimicking the mechanism of lysozyme-initiated hydrolysis. These donors were used to achieve chemoselective glycosidation of hex-2-enopyranosyl acetate and hexopyranosyl acetate, and synthesis of O-glycosidic linkages between highly deoxygenated sugars and tertiary alcohols.

Original language	English
Pages (from-to)	9039-9043
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2006.10.095
Publication status	Published - 2006 Dec 18

Keywords

Carbohydrates
Chemoselectivity
Deoxy sugar
Glycosidation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.10.095

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title = "An efficient glycosidation method using 2,3-unsaturated glycosyl donors",

abstract = "A novel class of 'armed' glycosyl donors containing a double bond at the C-2 position was designed by mimicking the mechanism of lysozyme-initiated hydrolysis. These donors were used to achieve chemoselective glycosidation of hex-2-enopyranosyl acetate and hexopyranosyl acetate, and synthesis of O-glycosidic linkages between highly deoxygenated sugars and tertiary alcohols.",

keywords = "Carbohydrates, Chemoselectivity, Deoxy sugar, Glycosidation",

author = "Kaname Sasaki and Shuichi Matsumura and Kazunobu Toshima",

note = "Funding Information: This research was supported in part by Grant-in-Aid for the 21st Century COE Program {\textquoteleft}KEIO Life Conjugated Chemistry{\textquoteright}, for Scientific Research on Priority Areas 18032068 and for JSPS Fellows 18∗6013 from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.",

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doi = "10.1016/j.tetlet.2006.10.095",

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T1 - An efficient glycosidation method using 2,3-unsaturated glycosyl donors

AU - Sasaki, Kaname

AU - Matsumura, Shuichi

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported in part by Grant-in-Aid for the 21st Century COE Program ‘KEIO Life Conjugated Chemistry’, for Scientific Research on Priority Areas 18032068 and for JSPS Fellows 18∗6013 from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

PY - 2006/12/18

Y1 - 2006/12/18

N2 - A novel class of 'armed' glycosyl donors containing a double bond at the C-2 position was designed by mimicking the mechanism of lysozyme-initiated hydrolysis. These donors were used to achieve chemoselective glycosidation of hex-2-enopyranosyl acetate and hexopyranosyl acetate, and synthesis of O-glycosidic linkages between highly deoxygenated sugars and tertiary alcohols.

AB - A novel class of 'armed' glycosyl donors containing a double bond at the C-2 position was designed by mimicking the mechanism of lysozyme-initiated hydrolysis. These donors were used to achieve chemoselective glycosidation of hex-2-enopyranosyl acetate and hexopyranosyl acetate, and synthesis of O-glycosidic linkages between highly deoxygenated sugars and tertiary alcohols.

KW - Carbohydrates

KW - Chemoselectivity

KW - Deoxy sugar

KW - Glycosidation

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M3 - Article

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SN - 0040-4039

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SP - 9039

EP - 9043

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

An efficient glycosidation method using 2,3-unsaturated glycosyl donors

Abstract

Keywords

ASJC Scopus subject areas

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