Research Advances in Functional Group-Directed Stereoselective Glycosylation

doi:10.6023/cjoc202204050

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3506-3529.DOI: 10.6023/cjoc202204050 Previous Articles Next Articles

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官能团导向立体选择性的糖苷化反应研究进展

孙阳星^a, 李彦芝^a, 曹燕来^b(), 王能中^a, 向少华^c^,^*(), 刘明国^a^,^*, 姚辉^a

^a三峡大学生物与制药学院中国轻工业功能酵母重点实验室天然产物研究与利用湖北省重点实验室湖北宜昌 443002
^b湖北广辰药业有限公司湖北宜昌 443002
^c南方科技大学深圳格拉布斯研究院化学系广东省催化重点实验室广东深圳 518055

收稿日期:2022-04-19 修回日期:2022-07-06 发布日期:2022-08-17
通讯作者: 向少华, 刘明国
基金资助:
高等学校学科创新引智计划(D20015); 湖北省自然科学基金(2020CFB205); 深圳市科创委基础研究自由探索(JCYJ20180305123508258)

Research Advances in Functional Group-Directed Stereoselective Glycosylation

Yangxing Sun^a, Yanzhi Li^a, Yanlai Cao^b(), Nengzhong Wang^a, Shaohua Xiang^c(), Mingguo Liu^a, Hui Yao^a

^aKey Laboratory of Natural Products Research and Development, Key Laboratory of Functional Yeast (China National Light Industry), College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002
^bHubei Guangchen Pharmaceutical Co. Ltd, Yichang, Hubei 443002
^cGuangdong Provincial Key Laboratory of Catalysis, Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055

Received:2022-04-19 Revised:2022-07-06 Published:2022-08-17
Contact: Shaohua Xiang, Mingguo Liu
Supported by:
Programme of Introducing Talents of Discipline to Universities (111 Project)(D20015); Natural Science Foundation of Hubei Province(2020CFB205); Shenzhen Special Funds(JCYJ20180305123508258)

Carbohydrates are not only an energy source for life activities, but also play a vital role in many physiological activities and drug development. Glycosylation is the core reaction of carbohydrate chemistry, and it is still a big challenge to develop a general stereoselective and efficent glycosylation method. The control of stereoselectivity is mainly carried out from three aspects: glycosyl donors, catalytic conditions and glycosyl acceptors. Among them, the development of glycosyl donors is the most concerned. The development of functional group of glycosyl donors on stereoselective regulation in the past decades is summarized. According to the way in which the functional groups participate in the glycosylation reactions, they are divided into neighboring-group participating groups, remote group participating groups, intramolecular aglycone delivery groups, coordination functional groups and hydrogen-bonding mediated groups.

Key words: carbohydrate, glycosylation reaction, functional group, stereoselective synthesis

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Yangxing Sun, Yanzhi Li, Yanlai Cao, Nengzhong Wang, Shaohua Xiang, Mingguo Liu, Hui Yao. Research Advances in Functional Group-Directed Stereoselective Glycosylation[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3506-3529.

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Fig. & Tab. 36

Scheme 1. Glycosides with medicinal value

Scheme 2. Synthesis of 1,2-trans-glycosides via the NGP effect of the C-2 acyl groups

Scheme 3. Synthesis of 1,2-trans-glycosides via the NGP effect of benzoyl/acetyl groups

Scheme 4. Stereoselectivity of products controlled by formation of decalin intermediates via chiral acyl functional groups

Scheme 5. Synthesis of 1,2-trans glycosides via the NGP effect of dialkyl phosphoryl functional groups

Scheme 6. Synthesis of 1,2-trans-glycosides by the NGP effect of DMNPA functional groups

Scheme 7. Stereoselective glycosylation based on cyclic sulfide ions

Scheme 8. Synthesis of 1,2-trans-glycosides via the NGP effect of the pyridylmethylene functional groups

Scheme 9. Dual orientation of 2-cyanophenyl ether functional groups

Scheme 10. Trapping experiment with 2-chlorobenzoic acid

Scheme 11. Synthesis of α-sialyl glycoside via the NGP effect of C-1 pyridylmethylene

Scheme 12. Three possible mechanisms for the formation of α-sialoside

Scheme 13. Synthesis of 1,2-trans-glycosides by 2-O-alkylmethyl/benzyl functional groups via the NGP effect

Scheme 14. Possible intermediates in the process of acyl functional groups exerting the RGP effect

Scheme 15. Synthesis of α-O-glycosides via RGP effect of the C-3 acyl groups of mannose

Scheme 16. RGP effect of DMNPA functional groups

Scheme 17. RGP effect of trichloroacetimide ester

Scheme 18. Synthesis of 1,2-cis-O-glycosides via the RGP effect of N-phenyltrifluoroacetimidyl groups

Scheme 19. Intramolecular aglycone delivery mediated by isopropenyl groups

Scheme 20. Intramolecular aglycone delivery mediated by dimethylsilyl chloride

Scheme 21. Intramolecular aglycone delivery mediated by dimethylsilyl groups

Scheme 22. Intramolecular aglycone delivery mediated by PMB and NAP

Scheme 23. Intramolecular aglycone delivery mediated by vinyl groups

Scheme 24. Intramolecular aglycone delivery mediated by borate ester

Scheme 25. Synthesis of α-O-glycosides by coordination directing of trichloroacetimidate functional groups

Scheme 26. Synthesis of α-O-glycosides by coordination directing of benzylimine functional groups

Scheme 27. Synthesis of O-glycosides by coordination directing of pyridate functional groups

Scheme 28. Synthesis of N-glycosides by coordination directing of pyridate functional groups

Scheme 29. Synthesis of α-C-glycosides by coordination directing of amidopyridine functional groups

Scheme 30. Synthesis of O-glycosides by coordination directing of carbonate functional groups

Scheme 31. Synthesis of N-glycosides and S-glycosides by coordination directing of carbonate functional groups

Scheme 32. Stereoselective synthesis of O-glycosides via hydrogen bonding of remote pyridine functional groups

Entry	Modification	α∶β
1	Heat at 50 ℃	1∶7.1
2	Added DMSO (1 equiv.)	1∶4.9
3	Excess DMTST (6 equiv.)	1∶9.8
4	Added tfoh (1 equiv.)	1∶8.1
5	Replace H with TMS	1∶2.0
6	4,6-O-benzylidene	1∶2.1

Table 1. Experiment of disrupting the H-bond

Scheme 33. Synthesis of arabinofuranosyl β-O-glycosides via hydrogen bonding of quinalidate functional groups

Scheme 34. Stereoselective synthesis of O-glycosides via hydrogen bonding of DPPA functional groups

Scheme 35. Synthesis of β-O-glycosides via hydrogen bonding between sulfonamide functional groups and exogenous nucleophiles

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官能团导向立体选择性的糖苷化反应研究进展

Research Advances in Functional Group-Directed Stereoselective Glycosylation

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