Efficient glycosylation with glycosyl ortho-allylbenzoates as donors

Haijing Liang; Lixia Ma; Changwei Li; Qiang Peng; Zhaoyan Wang; Zhan xin Zhang; Lan Yu; Huanxiang Liu; Fengli An; Weihua Xue

doi:10.1016/j.tetlet.2018.11.061

Efficient glycosylation with glycosyl ortho-allylbenzoates as donors

Haijing Liang, Lixia Ma, Changwei Li, Qiang Peng, Zhaoyan Wang, Zhan xin Zhang, Lan Yu, Huanxiang Liu, Fengli An, Weihua Xue

Lanzhou University

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

6 Citations (Scopus)

Abstract

Glycosylation reactions are significant as they provide access to model compounds that are useful for elucidating biochemical pathways. Herein, we describe the development of glycosyl ortho-alkynylbenzoates as novel, bench-top stable, and readily available glycosyl donors. Glycosylation is promoted by inexpensive trimethylsilyl triflate (TMSOTf) in combination with N-iodosuccinimide (NIS) under mild reaction conditions; hence, the novel glycosyl donors are promising reagents for the synthesis of glycosides.

Original language	English
Pages (from-to)	84-87
Number of pages	4
Journal	Tetrahedron Letters
Volume	60
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2018.11.061
Publication status	Published - 3 Jan 2019
Externally published	Yes

Keywords

Glycosyl ortho-allylbenzoates
Glycosylation
Lactonisation
NIS

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10.1016/j.tetlet.2018.11.061

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title = "Efficient glycosylation with glycosyl ortho-allylbenzoates as donors",

abstract = "Glycosylation reactions are significant as they provide access to model compounds that are useful for elucidating biochemical pathways. Herein, we describe the development of glycosyl ortho-alkynylbenzoates as novel, bench-top stable, and readily available glycosyl donors. Glycosylation is promoted by inexpensive trimethylsilyl triflate (TMSOTf) in combination with N-iodosuccinimide (NIS) under mild reaction conditions; hence, the novel glycosyl donors are promising reagents for the synthesis of glycosides.",

keywords = "Glycosyl ortho-allylbenzoates, Glycosylation, Lactonisation, NIS",

author = "Haijing Liang and Lixia Ma and Changwei Li and Qiang Peng and Zhaoyan Wang and Zhang, {Zhan xin} and Lan Yu and Huanxiang Liu and Fengli An and Weihua Xue",

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T1 - Efficient glycosylation with glycosyl ortho-allylbenzoates as donors

AU - Liang, Haijing

AU - Ma, Lixia

AU - Li, Changwei

AU - Peng, Qiang

AU - Wang, Zhaoyan

AU - Zhang, Zhan xin

AU - Yu, Lan

AU - Liu, Huanxiang

AU - An, Fengli

AU - Xue, Weihua

PY - 2019/1/3

Y1 - 2019/1/3

N2 - Glycosylation reactions are significant as they provide access to model compounds that are useful for elucidating biochemical pathways. Herein, we describe the development of glycosyl ortho-alkynylbenzoates as novel, bench-top stable, and readily available glycosyl donors. Glycosylation is promoted by inexpensive trimethylsilyl triflate (TMSOTf) in combination with N-iodosuccinimide (NIS) under mild reaction conditions; hence, the novel glycosyl donors are promising reagents for the synthesis of glycosides.

AB - Glycosylation reactions are significant as they provide access to model compounds that are useful for elucidating biochemical pathways. Herein, we describe the development of glycosyl ortho-alkynylbenzoates as novel, bench-top stable, and readily available glycosyl donors. Glycosylation is promoted by inexpensive trimethylsilyl triflate (TMSOTf) in combination with N-iodosuccinimide (NIS) under mild reaction conditions; hence, the novel glycosyl donors are promising reagents for the synthesis of glycosides.

KW - Glycosyl ortho-allylbenzoates

KW - Glycosylation

KW - Lactonisation

KW - NIS

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DO - 10.1016/j.tetlet.2018.11.061

M3 - Article

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SN - 0040-4039

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SP - 84

EP - 87

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

Efficient glycosylation with glycosyl ortho-allylbenzoates as donors

Abstract

Keywords

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