Investigation of the remote acyl group participation in glycosylation from conformational perspectives by using trichloroacetimidate as the acetyl surrogate

Author:

Xu Ke12345,Man Qingmin67589,Zhang Yang12345,Guo Jia12345,Liu Yichu12345,Fu Zunyun1011589,Zhu Yueyue12345,Li Yingxia12345,Zheng Mingyue891245ORCID,Ding Ning12345ORCID

Affiliation:

1. Department of Medicinal Chemistry

2. School of Pharmacy

3. Fudan University

4. Shanghai 201203

5. China

6. University of Science and Technology of China

7. Hefei

8. State Key Laboratory of Drug Research

9. Shanghai Institute of Materia Medica

10. Nanjing University of Chinese Medicine

11. Jiangsu

12. Chinese Academy of Sciences

Abstract

The remote acyl group participation in glycosylation was studied by using trichloroacetimidate as the acetyl surrogate. The bridging participation intermediates were systematically trapped, and DFT calculations were applied to explain the results.

Funder

National Key New Drug Creation and Manufacturing Program, Ministry of Science and Technology

National Natural Science Foundation of China

Chinese Academy of Sciences

Shanghai Municipal Human Resources and Social Security Bureau

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Reference46 articles.

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2. O-Glycosylation methods in the total synthesis of complex natural glycosides

3. B. S. Komarova , N. E.Ustyuzhanina , Y. E.Tsvetkov and N. E.Nifantiev , in Modern Synthetic Methods in Carbohydrate Chemistry: From Mono-saccharides to Complex Glycoconjugates , ed. D. B. Werz and S. Vidal , Wiley-VCH Verlag GmbH & Co. KGaA , 1st edn, 2014 , ch. 5, p. 2014

4. Catching elusive glycosyl cations in a condensed phase with HF/SbF5 superacid

5. Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry

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