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

10 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",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2019",

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doi = "10.1016/j.tetlet.2018.11.061",

language = "English",

volume = "60",

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TY - JOUR

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

UR - https://www.scopus.com/pages/publications/85057164222

U2 - 10.1016/j.tetlet.2018.11.061

DO - 10.1016/j.tetlet.2018.11.061

M3 - Article

AN - SCOPUS:85057164222

SN - 0040-4039

VL - 60

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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