官能团导向立体选择性的糖苷化反应研究进展

doi:10.6023/cjoc202204050

有机化学 ›› 2022, Vol. 42 ›› Issue (11): 3506-3529.DOI: 10.6023/cjoc202204050 上一篇下一篇

综述与进展

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)

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摘要/Abstract

糖类化合物不仅是生命活动的能量来源, 还在许多细胞信号传导和药物研发中发挥着至关重要的作用. 糖化学的核心是糖苷化反应, 而开发一种通用、高效的立体选择性糖苷化方法仍是一大挑战. 目前主要从糖供体、催化条件以及糖受体三个方面进行立体选择性糖苷化反应研究, 其中研究最多的是糖供体的开发. 主要综述了近十年来糖供体的官能团对糖苷化立体选择性调控的发展, 根据官能团参与糖苷化反应的方式可将其分为五大类: 邻基参与型官能团、远程参与型官能团、分子内苷元传递型官能团、与催化剂配位型官能团及氢键作用型官能团.

关键词: 糖类化合物, 糖苷化反应, 官能团, 立体选择性合成

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

引用此文

孙阳星, 李彦芝, 曹燕来, 王能中, 向少华, 刘明国, 姚辉. 官能团导向立体选择性的糖苷化反应研究进展[J]. 有机化学, 2022, 42(11): 3506-3529.

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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图/表 36

图式1. 具有药用价值的糖苷类化合物

Scheme 1. Glycosides with medicinal value

图式2. 通过C-2酰基的邻基参与效应合成1,2-反式糖苷

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

图式3. 通过苯甲酰基/乙酰基的邻基参与效应合成1,2-反式糖苷

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

图式4. 通过手性酰基官能团形成十氢萘中间体控制产物的立体选择性

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

图式5. 通过二烷基磷酰基官能团的邻基参与效应合成1,2-反式糖苷

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

图式6. 通过DMNPA官能团邻基团参与效应合成1,2-反式糖苷

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

图式7. 基于环硫离子的立体选择性糖苷化

Scheme 7. Stereoselective glycosylation based on cyclic sulfide ions

图式8. 通过吡啶亚甲基官能团的邻基参与效应合成1,2-反式糖苷

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

图式9. 2-氰基苯醚官能团的双重导向性

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

图式10. 采用2-氯苯甲酸捕获中间体的实验

Scheme 10. Trapping experiment with 2-chlorobenzoic acid

图式11. 通过C-1吡啶亚甲基的邻基团参与效应合成α-唾液酸苷

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

图式12. 三种生成α-唾液酸苷的可能机理

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

图式13. 通过2-烷氧基甲基/苄基官能团的邻基团参与效应合成1,2-反式糖苷

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

图式14. 酰基类官能团在发挥远程参与效应过程中可能存在的中间体

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

图式15. 通过甘露糖C-3位酰基的远程参与效应合成α-O-糖苷

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

图式16. DMNPA官能团的远程参与效应

Scheme 16. RGP effect of DMNPA functional groups

图式17. 三氯乙酰亚胺酯的远程参与效应

Scheme 17. RGP effect of trichloroacetimide ester

图式18. 通过N-苯基三氟乙酰亚胺基的远程参与效应合成1,2-顺式-O-糖苷

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

图式19. 异丙烯基介导的分子内苷元传递

Scheme 19. Intramolecular aglycone delivery mediated by isopropenyl groups

图式20. 二甲基氯硅基介导的分子内苷元传递

Scheme 20. Intramolecular aglycone delivery mediated by dimethylsilyl chloride

图式21. 二甲基硅基介导的分子内苷元传递

Scheme 21. Intramolecular aglycone delivery mediated by dimethylsilyl groups

图式22. PMB和NAP介导的分子内苷元传递

Scheme 22. Intramolecular aglycone delivery mediated by PMB and NAP

图式23. 乙烯基介导的分子内苷元传递

Scheme 23. Intramolecular aglycone delivery mediated by vinyl groups

图式24. 硼酸酯介导的分子内苷元传递

Scheme 24. Intramolecular aglycone delivery mediated by borate ester

图式25. 通过三氯乙酰亚胺酯官能团的配位导向作用合成α-O-糖苷

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

图式26. 通过苄亚胺官能团的配位导向作用合成α-O-糖苷

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

图式27. 通过吡啶酸酯官能团的配位导向作用合成O-糖苷

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

图式28. 通过吡啶酸酯官能团的配位导向作用合成N-糖苷

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

图式29. 通过酰胺基吡啶官能团的配位导向作用合成α-C-糖苷

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

图式 30. 通过碳酸酯官能团的配位导向作用合成O-糖苷

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

图式31. 通过碳酸酯官能团的配位导向作用合成N-糖苷和S-糖苷

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

图式32. 通过远程吡啶官能团的氢键作用立体选择性地合成O-糖苷

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

表1. 氢键破坏实验

Table 1. Experiment of disrupting the H-bond

图式33. 通过喹哪啶酸酯官能团的氢键作用合成阿拉伯呋喃糖β-O-糖苷

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

图式34. 通过DPPA官能团的氢键作用立体选择性地合成O-糖苷

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

图式35. 通过磺酰胺官能团与外源亲核试剂间的氢键作用合成β-O-糖苷

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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