三异丙基甲硅烷基与两种氟代类似物的相对反应活性比较。
Comparison of the Relative Reactivities of the Triisopropylsilyl Group With Two Fluorous Analogs.
作者信息
Sancho Amador Garcia, Wang Xiao, Sui Bin, Curran Dennis
机构信息
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
出版信息
Adv Synth Catal. 2009 May 1;351(7-8):1035-1040. doi: 10.1002/adsc.200900061.
Abstract
The relative stabilities of two fluorous analogs, diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silyl and diisopropyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadeca-fluoroundecyl)silyl [C(8)F(17)(CH(2))(n)Si(i-Pr)(2), where n = 2 or 3], of the standard triisopropylsilyl (TIPS) group are compared in the setting of alcohol protection. The fluorous silyl groups can be installed under standard conditions in comparable yields to the TIPS group, but the derived fluorous silyl ethers are more labile than TIPS ethers towards cleavage by both acids and fluoride.
摘要
在醇保护的背景下，比较了标准三异丙基甲硅烷基（TIPS）基团的两种氟代类似物，二异丙基（3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10 - 十七氟癸基）甲硅烷基和二异丙基 - （4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11 - 十七氟十一烷基）甲硅烷基[C(8)F(17)(CH(2))(n)Si(i-Pr)(2)，其中n = 2或3]的相对稳定性。氟代甲硅烷基团可以在标准条件下以与TIPS基团相当的产率引入，但衍生的氟代甲硅烷基醚在酸和氟化物的作用下比TIPS醚更不稳定，更容易发生裂解。
相似文献
1
Comparison of the Relative Reactivities of the Triisopropylsilyl Group With Two Fluorous Analogs.三异丙基甲硅烷基与两种氟代类似物的相对反应活性比较。
Adv Synth Catal. 2009 May 1;351(7-8):1035-1040. doi: 10.1002/adsc.200900061.
2
Synthesis and properties of fluorous benzoquinones and their application in deprotection of silyl ethers.氟代苯醌的合成、性质及其在硅醚脱保护中的应用。
Org Biomol Chem. 2014 Aug 7;12(29):5442-7. doi: 10.1039/c4ob00783b.
3
Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines.轻、中、重氟代三芳基膦在三芳基膦的典型反应中表现出与三苯基膦相当的反应活性。
J Org Chem. 2005 Apr 29;70(9):3716-9. doi: 10.1021/jo050116j.
4
Parallel synthesis and study of fluorous biphasic partition coefficients of 1H,1H,2H,2H-perfluoroalkylsilyl derivatives of triphenylphosphine: a statistical approach.三苯基膦的1H,1H,2H,2H-全氟烷基硅烷基衍生物的氟两相分配系数的平行合成与研究：一种统计方法。
J Comb Chem. 2004 May-Jun;6(3):363-74. doi: 10.1021/cc049959z.
5
Synthesis and properties of a novel family of fluorous triphenylphosphine derivatives.新型含氟三苯基膦衍生物家族的合成与性质
J Org Chem. 2000 Jun 30;65(13):3885-93. doi: 10.1021/jo991548v.
6
Fluorination of silyl prosthetic groups by fluorine mediated silyl ether linker cleavage: a concept study with conditions applicable in radiofluorination.通过氟介导的硅醚连接键裂解实现硅烷基取代基的氟化：一项适用于放射性氟化条件的概念研究。
EJNMMI Radiopharm Chem. 2022 Jun 25;7(1):15. doi: 10.1186/s41181-022-00167-y.
7
Synthesis of the Lewis a trisaccharide based on an anomeric silyl fluorous tag.基于异头硅基氟标签的Lewis a三糖的合成。
Org Lett. 2004 Nov 11;6(23):4195-8. doi: 10.1021/ol048474g.
8
Structure and reactivity of bis(silyl) dihydride complexes (PMe(3))(3)Ru(SiR(3))(2)(H)(2): model compounds and real intermediates in a dehydrogenative C-Si bond forming reaction.双（硅基）二氢配合物(PMe(3))(3)Ru(SiR(3))(2)(H)(2)的结构与反应活性：脱氢C-Si键形成反应中的模型化合物与实际中间体
J Am Chem Soc. 2003 Jul 23;125(29):8936-48. doi: 10.1021/ja035916v.
9
Fluorous triphasic reactions: transportative deprotection of fluorous silyl ethers with concomitant purification.氟相三相反应：氟代甲硅烷基醚的迁移性脱保护及同步纯化
J Am Chem Soc. 2001 Oct 17;123(41):10119-20. doi: 10.1021/ja011716c.
10
A novel, chemoselective and efficient microwave-assisted deprotection of silyl ethers with selectfluor.一种新型的、化学选择性的和高效的微波辅助脱保护硅醚的方法，使用的是 Selectfluor。
J Org Chem. 2009 Mar 6;74(5):2179-82. doi: 10.1021/jo802494t.
引用本文的文献
1
Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.2009年药物发现与化学生物学化学文库综合调查
J Comb Chem. 2010 Nov 8;12(6):765-806. doi: 10.1021/cc100128w. Epub 2010 Oct 5.
2
Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers.通过对四个候选立体异构体的混合物合成来确定 petrocortyne A 的结构。
J Org Chem. 2010 May 7;75(9):2942-54. doi: 10.1021/jo100115h.
本文引用的文献
1
Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2007.2007年药物发现与化学生物学化学文库综合调查
J Comb Chem. 2008 Nov-Dec;10(6):753-802. doi: 10.1021/cc800119z.
2
Synthetic applications of fluorous solid-phase extraction (F-SPE).氟相固相萃取（F-SPE）的合成应用。
Tetrahedron. 2006 Dec 18;62(51):11837-11865. doi: 10.1016/j.tet.2006.08.051.
3
Confirmation of the stereostructure of (+)-cytostatin by fluorous mixture synthesis of four candidate stereoisomers.通过四种候选立体异构体的氟代混合物合成对（+）-细胞抑制素立体结构的确认。
Angew Chem Int Ed Engl. 2008;47(6):1130-3. doi: 10.1002/anie.200704893.
4
Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers.通过四种候选立体异构体的氟代混合物合成对拉古纳吡喃酮B进行结构归属
J Am Chem Soc. 2006 Nov 1;128(43):14200-5. doi: 10.1021/ja064812s.
5
Total synthesis of a 28-member stereoisomer library of murisolins.鼠李素28个成员的立体异构体文库的全合成。
J Am Chem Soc. 2006 Jul 26;128(29):9561-73. doi: 10.1021/ja061801q.
6
Fluorous (trimethylsilyl)ethanol: a new reagent for carboxylic acid tagging and protection in peptide synthesis.氟代（三甲基硅基）乙醇：肽合成中用于羧酸标记和保护的新型试剂。
J Org Chem. 2006 Apr 14;71(8):3299-302. doi: 10.1021/jo052569u.
7
Structure elucidation of Sch 725674 from Aspergillus sp.来自曲霉属真菌的Sch 725674的结构解析
J Antibiot (Tokyo). 2005 Aug;58(8):535-8. doi: 10.1038/ja.2005.74.
8
Quasienantiomers and quasiracemates: new tools for identification, analysis, separation, and synthesis of enantiomers.准对映体和准外消旋体：对映体鉴定、分析、分离及合成的新工具。
Chemistry. 2005 Aug 19;11(17):4866-80. doi: 10.1002/chem.200500076.
9
Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines.轻、中、重氟代三芳基膦在三芳基膦的典型反应中表现出与三苯基膦相当的反应活性。
J Org Chem. 2005 Apr 29;70(9):3716-9. doi: 10.1021/jo050116j.
10
Synthesis of the Lewis a trisaccharide based on an anomeric silyl fluorous tag.基于异头硅基氟标签的Lewis a三糖的合成。
Org Lett. 2004 Nov 11;6(23):4195-8. doi: 10.1021/ol048474g.
Zotero 插件