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Photo-/Electro-Driven Carbohydrate-Based Reactions

Hanyu Zhang , Meng Liu , Xia Wu , Miao Liu , Decai Xiong , Xinshan Ye

Progress in Chemistry ›› 2020, Vol. 32 ›› Issue (11) : 1804 -1823.

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Progress in Chemistry ›› 2020, Vol. 32 ›› Issue (11) : 1804-1823 DOI: 10.7536/PC200608
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Photo-/Electro-Driven Carbohydrate-Based Reactions
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Abstract

Carbohydrates are the most abundant organic compounds in nature, which play essential roles in the fields of medicine, materials, energy and environment. Due to the specific characteristic of high polarity, sophisticated structure and microheterogeneity, it is particularly difficult to separate, purify and synthesize carbohydrates. At present, the acquirement of carbohydrate compounds with homogeneous and diverse structures and in high purity mainly depends on chemical synthesis. However, the effective synthesis of carbohydrates has become a bottleneck of restricting the progress of glycoscience. The development of new methods and strategies for the synthesis of carbohydrates is the core topic in carbohydrate chemistry. The reaction driven by photon/electron energy usually takes place under mild conditions, which meets the requirements of green chemistry and sustainable development, and is also one of the research frontiers in modern organic synthesis. Nowadays, with the development of photo-/electro-synthetic technology, many achievements have been made in carbohydrate-based reactions driven by photon/electron energy. In view of reaction type, mechanism and status, this review will systematically summarize the latest advances on photo-/electro-driven reactions in the synthesis of carbohydrates. This review will also analyze the current challenges and new opportunities of carbohydrate-based reactions driven by photon/electron energy.

Contents

1 Introduction

2 Photo-/electro-driven glycosylation

2.1 Thioglycosides as the donors

2.2 Selenoglycosides as the donors

2.3 Telluroglycosides as the donors

2.4 O-glycosides as the donors

2.5 Glycosyl trichloroacetimidates as the donors

2.6 Glycosyl halides as the donors

2.7 Glycals as the donors

3 Photo-driven modifications of carbohydrates

3.1 Photo-driven reductive defunctionalization

3.2 Photo-driven halogenation

3.3 Photo-driven functionalization on the anomeric O-/S-atoms

3.4 Photo-driven decarboxylation

3.5 Photo-driven isomerization

4 Conclusion and outlook

Graphical abstract

Keywords

carbohydrate / carbohydrate chemistry / glycosylation / photo-glycosylation / electro-glycosylation

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Hanyu Zhang, Meng Liu, Xia Wu, Miao Liu, Decai Xiong, Xinshan Ye. Photo-/Electro-Driven Carbohydrate-Based Reactions. Progress in Chemistry, 2020, 32(11): 1804-1823 DOI:10.7536/PC200608

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References

Funding

the National Key Research and Development Program of China(2018YFA0507602)

the National Natural Science Foundation of China(21738001)

and the National New Drug Innovation Major Project of China(2019ZX09301106)

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