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Temporary ether protecting groups at the anomeric center in complex carbohydrate synthesis
1Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing, China.
Advances in Carbohydrate Chemistry and Biochemistry
|October 2, 2020
Summary
Choosing the right temporary protecting group for carbohydrate synthesis is crucial. This review covers etherate protecting groups, detailing their formation, cleavage, and use in complex carbohydrate synthesis.
Area of Science:
- Organic Chemistry
- Carbohydrate Chemistry
- Synthetic Chemistry
Background:
- Temporary protecting groups are essential for carbohydrate synthesis, particularly at the anomeric center.
- The anomeric protecting group must be stable throughout synthesis and selectively removable.
- Etherate groups are widely employed, including allyl, p-methoxyphenyl (MP), benzyl, p-methoxybenzyl (PMB), and silyl ethers.
Purpose of the Study:
- To provide a comprehensive review of temporary protecting groups used in carbohydrate synthesis.
- To detail the formation, cleavage, and applications of various etherate protecting groups.
- To highlight the importance of chemoselective cleavage in complex carbohydrate synthesis.
Main Methods:
- Review of existing literature on anomeric protecting groups.
- Analysis of formation and cleavage conditions for different etherate protecting groups.
- Compilation of examples showcasing the application of these groups in complex carbohydrate synthesis.
Main Results:
- Etherate groups (allyl, MP, benzyl, PMB, silyl ethers) are versatile for anomeric protection.
- Specific conditions for the formation and selective cleavage of these groups are presented.
- Successful applications in the synthesis of diverse complex carbohydrates are demonstrated.
Conclusions:
- The selection of an appropriate anomeric temporary protecting group is critical for successful carbohydrate synthesis.
- Etherate protecting groups offer a range of options with distinct properties for chemoselective manipulation.
- This review serves as a valuable resource for chemists synthesizing complex carbohydrates.
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