一种用于叔丁基二苯基硅醚裂解的高效可回收催化剂。
An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers.
机构信息
Key Lab of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.
出版信息
Carbohydr Res. 2012 Jun 1;354:6-20. doi: 10.1016/j.carres.2012.02.021. Epub 2012 Mar 1.
PMID:22565030
Abstract
An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled.
摘要
报道了一种在硅胶负载的三氟磺酸作用下，高效、选择性和环境友好的脱除叔丁基二苯基硅醚保护基的方法。在乙腈中，各种类型的其他保护基存在下，该非均相反应可以顺利地将来源于碳水化合物和皂苷残基的叔丁基二苯基硅醚以良好到优秀的产率脱去保护基。该反应不需要进行水相处理，并且负载型催化剂可以很容易地回收。
相似文献
1
An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers.一种用于叔丁基二苯基硅醚裂解的高效可回收催化剂。
Carbohydr Res. 2012 Jun 1;354:6-20. doi: 10.1016/j.carres.2012.02.021. Epub 2012 Mar 1.
2
A facile, catalytic, and environmentally benign method for selective deprotection of tert-butyldimethylsilyl ether mediated by phosphomolybdic acid supported on silica gel.一种简便、催化且环境友好的方法，用于硅胶负载的磷钼酸介导的叔丁基二甲基甲硅烷基醚的选择性脱保护。
J Org Chem. 2005 May 27;70(11):4520-3. doi: 10.1021/jo0502697.
3
Selective deprotection of terminal isopropylidene acetals and trityl ethers using HClO4 supported on silica gel.使用负载在硅胶上的高氯酸对末端异亚丙基缩醛和三苯甲基醚进行选择性脱保护。
Carbohydr Res. 2005 Jul 4;340(9):1661-7. doi: 10.1016/j.carres.2005.04.005.
4
Sc(OTf)3-mediated silylation of hydroxy functional groups on a solid surface: a catalytic grafting method operating at room temperature.三氟甲磺酸钪介导的固体表面羟基官能团的硅烷化反应：一种在室温下进行的催化接枝方法。
Angew Chem Int Ed Engl. 2008;47(1):109-12. doi: 10.1002/anie.200703112.
5
Highly efficient etherification of silanes by using a gold nanoparticle catalyst: remarkable effect of O(2).金纳米粒子催化剂高效醚化硅烷：O(2)的显著作用。
Chemistry. 2013 Oct 18;19(43):14398-402. doi: 10.1002/chem.201302807. Epub 2013 Sep 24.
6
Efficient room-temperature O-silylation of alcohols using a SBA-15-supported cobalt(II) nanocatalyst.使用负载型钴(II)纳米催化剂的 SBA-15 高效室温醇的 O-硅烷化反应。
Chem Biodivers. 2012 Sep;9(9):1823-8. doi: 10.1002/cbdv.201200071.
7
Metal-catalyzed rearrangement of homoallylic ethers to silylmethyl allylic silanes in the presence of a Di-tert-butylsilylene source.在二叔丁基硅烯源存在下，金属催化的高烯丙基醚重排为甲硅烷基甲基烯丙基硅烷。
Org Lett. 2005 Nov 24;7(24):5531-3. doi: 10.1021/ol052456x.
8
9-Thiourea Cinchona alkaloid supported on mesoporous silica as a highly enantioselective, recyclable heterogeneous asymmetric catalyst.负载于介孔二氧化硅上的9-硫脲金鸡纳生物碱作为一种高对映选择性、可循环使用的多相不对称催化剂。
Chem Commun (Camb). 2008 May 28(20):2355-7. doi: 10.1039/b800640g. Epub 2008 Mar 17.
9
Catalytic asymmetric Simmons-Smith cyclopropanation of silyl enol ethers. Efficient synthesis of optically active cyclopropanol derivatives.硅烯醇醚的催化不对称西蒙斯-史密斯环丙烷化反应。光学活性环丙醇衍生物的高效合成。
Org Lett. 2006 Jun 22;8(13):2827-9. doi: 10.1021/ol0609659.
10
Simple, efficient, and selective deprotection of phenolic methoxymethyl ethers using silica-supported sodium hydrogen sulfate as a heterogeneous catalyst.使用二氧化硅负载的硫酸氢钠作为多相催化剂对酚类甲氧基甲基醚进行简单、高效且选择性的脱保护。
J Org Chem. 2003 Sep 5;68(18):7101-3. doi: 10.1021/jo030088+.
引用本文的文献
1
Strategies to Develop Na,K-ATPase-α4 Inhibitors as Male Contraceptives.开发钠钾ATP酶-α4抑制剂作为男性避孕药的策略。
Int J Mol Sci. 2025 Jun 12;26(12):5646. doi: 10.3390/ijms26125646.
2
Selective Acetylation of Unprotected Thioglycosides and Fully Unprotected Monosaccharides with Candida antarctica Lipase‑B.利用南极假丝酵母脂肪酶B对未保护的硫代糖苷和完全未保护的单糖进行选择性乙酰化反应。
ACS Omega. 2025 May 7;10(19):20047-20053. doi: 10.1021/acsomega.5c02467. eCollection 2025 May 20.
3
Direct Synthesis of Glycosyl Chlorides from Thioglycosides.直接从硫代糖苷合成糖苷氯化物。
J Org Chem. 2024 May 17;89(10):6865-6876. doi: 10.1021/acs.joc.4c00244. Epub 2024 Apr 26.
4
Stereocontrolled α-Galactosylation under Cooperative Catalysis.协同催化下的立体控制α-半乳糖基化反应
J Org Chem. 2020 Dec 18;85(24):15936-15944. doi: 10.1021/acs.joc.0c01279. Epub 2020 Oct 16.
5
Synthesis of high-mannose oligosaccharides containing mannose-6-phosphate residues using regioselective glycosylation.使用区域选择性糖基化合成含6-磷酸甘露糖残基的高甘露糖型寡糖。
Carbohydr Res. 2018 Sep;467:23-32. doi: 10.1016/j.carres.2018.07.005. Epub 2018 Jul 31.
Zotero 插件