• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

用于TBAF介导的去硅基化反应的操作简单且高效的后处理程序：在海兔毒素合成中的应用。

Operationally simple and efficient workup procedure for TBAF-mediated desilylation: application to halichondrin synthesis.

作者信息

Kaburagi Yosuke, Kishi Yoshito

机构信息

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

出版信息

Org Lett. 2007 Feb 15;9(4):723-6. doi: 10.1021/ol063113h.

DOI:10.1021/ol063113h
PMID:17286380
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2519602/
Abstract

An operationally simple and efficient workup method for tetrabutylammonium fluoride (TBAF)-mediated t-butyldimethylsilyl (TBS) deprotection has been developed. The procedure includes addition of a sulfonic acid resin and calcium carbonate, followed by filtration and evaporation. This method eliminates the tedious aqueous-phase extraction process to remove excess TBAF and materials derived from TBAF, thereby making the protocol highly amenable to multiple TBS deprotections. Its efficiency and usefulness were demonstrated by using the transformation of 1a to 3a in the halichondrin synthesis. [reaction: see text].

摘要

已开发出一种用于四丁基氟化铵（TBAF）介导的叔丁基二甲基硅基（TBS）脱保护的操作简单且高效的后处理方法。该步骤包括加入磺酸树脂和碳酸钙，然后过滤和蒸发。此方法省去了去除过量TBAF及其衍生材料的繁琐水相萃取过程，从而使该方案非常适合多次TBS脱保护。通过在海兔毒素合成中使用1a到3a的转化证明了其效率和实用性。[反应：见正文]

相似文献

1
Operationally simple and efficient workup procedure for TBAF-mediated desilylation: application to halichondrin synthesis.用于TBAF介导的去硅基化反应的操作简单且高效的后处理程序：在海兔毒素合成中的应用。
Org Lett. 2007 Feb 15;9(4):723-6. doi: 10.1021/ol063113h.
2
Effect of excess water on the desilylation of oligoribonucleotides using tetrabutylammonium fluoride.过量水对使用四丁基氟化铵进行寡核糖核苷酸脱硅反应的影响。
Nucleic Acids Res. 1993 Oct 11;21(20):4739-41. doi: 10.1093/nar/21.20.4739.
3
A mixed resin bed for the quenching and purification of tetrabutylammonium fluoride mediated desilylating reactions.用于淬灭和纯化四丁基氟化铵介导的脱硅反应的混合树脂床。
Bioorg Med Chem Lett. 1998 Sep 8;8(17):2391-4. doi: 10.1016/s0960-894x(98)00432-6.
4
Halichondrin B: synthesis of the C(1)-C(15) subunit.海兔毒素B：C(1)-C(15)亚基的合成
J Org Chem. 2000 Jun 30;65(13):4070-87. doi: 10.1021/jo000140r.
5
Removal of t-butyldimethylsilyl protection in RNA-synthesis. Triethylamine trihydrofluoride (TEA, 3HF) is a more reliable alternative to tetrabutylammonium fluoride (TBAF).RNA合成中叔丁基二甲基硅基保护基的去除。三乙胺三氢氟酸盐（TEA·3HF）是氟化四丁铵（TBAF）更可靠的替代物。
Nucleic Acids Res. 1994 Jun 25;22(12):2430-1. doi: 10.1093/nar/22.12.2430.
6
An improved procedure for the synthesis of dehydroamino acids and dehydropeptides from the carbonate derivatives of serine and threonine using tetrabutylammonium fluoride.用四丁基氟化铵由丝氨酸和苏氨酸的碳酸盐衍生物合成脱氢氨基酸和脱氢肽的改进方法。
J Pept Sci. 2010 Mar;16(3):123-5. doi: 10.1002/psc.1210.
7
Total synthesis of halichondrin A, the missing member in the halichondrin class of natural products.卤虫内酯 A 的全合成，卤虫内酯类天然产物中缺失的成员。
J Am Chem Soc. 2014 Apr 2;136(13):5171-6. doi: 10.1021/ja5013307. Epub 2014 Mar 19.
8
Anhydrous tetrabutylammonium fluoride.无水四丁基氟化铵
J Am Chem Soc. 2005 Feb 23;127(7):2050-1. doi: 10.1021/ja0440497.
9
Synthesis of pulvinic derivatives via TBAF-mediated regioselective opening of an unsymmetrical monoaromatic pulvinic dilactone.通过 TBAF 介导的非对称单芳基戊二内酯的区域选择性开环反应合成戊二酰衍生物。
J Org Chem. 2008 Dec 5;73(23):9490-3. doi: 10.1021/jo801817s.
10
Safe deprotection strategy for the tert-butyldimethylsilyl (TBS) group during RNA synthesis.RNA合成过程中叔丁基二甲基硅烷基（TBS）基团的安全脱保护策略。
Curr Protoc Nucleic Acid Chem. 2012 Jun;Chapter 3:Unit3.21. doi: 10.1002/0471142700.nc0321s49.

引用本文的文献

1
α-Selective Glycosidation of the Rare Sugar d-Tagatofuranose and the Synthesis of α-d-Tagatofuranosylceramide.稀有糖d-塔格呋喃糖的α-选择性糖基化及α-d-塔格呋喃糖基神经酰胺的合成
Int J Mol Sci. 2025 Aug 30;26(17):8459. doi: 10.3390/ijms26178459.
2
Generality-oriented optimization of enantioselective aminoxyl radical catalysis.面向一般性的对映选择性氮氧自由基催化的优化。
Science. 2023 May 19;380(6646):706-712. doi: 10.1126/science.adf6177. Epub 2023 May 18.
3
Efficient access to 3'--phosphoramidite derivatives of tRNA related -threonylcarbamoyladenosine (tA) and 2-methylthio- -threonylcarbamoyladenosine (mstA).高效获取与苏氨甲酰腺苷（tA）和2-甲硫基-苏氨甲酰腺苷（mstA）相关的tRNA的3'-亚磷酰胺衍生物。
RSC Adv. 2021 Jan 7;11(4):1992-1999. doi: 10.1039/d0ra09803e. eCollection 2021 Jan 6.
4
Organic Thermoelectric Materials as the Waste Heat Remedy.有机热电材料——余热的补救措施。
Molecules. 2022 Feb 2;27(3):1016. doi: 10.3390/molecules27031016.
5
C5-Substituted 2-Selenouridines Ensure Efficient Base Pairing with Guanosine; Consequences for Reading the NNG-3' Synonymous mRNA Codons.C5-取代的 2-硒代尿苷确保与鸟苷的有效碱基配对；对阅读 NNG-3'同义 mRNA 密码子的影响。
Int J Mol Sci. 2020 Apr 20;21(8):2882. doi: 10.3390/ijms21082882.
6
Overcoming synthetic challenges in targeting coenzyme A biosynthesis with the antimicrobial natural product CJ-15,801.利用抗微生物天然产物CJ-15,801应对靶向辅酶A生物合成中的合成挑战。
Medchemcomm. 2019 Oct 17;10(12):2118-2125. doi: 10.1039/c9md00312f. eCollection 2019 Dec 1.
7
Kinetically controlled E-selective catalytic olefin metathesis.动力学控制的E-选择性催化烯烃复分解反应
Science. 2016 Apr 29;352(6285):569-75. doi: 10.1126/science.aaf4622.
8
Capturing Biological Activity in Natural Product Fragments by Chemical Synthesis.通过化学合成捕捉天然产物片段中的生物活性。
Angew Chem Int Ed Engl. 2016 Mar 14;55(12):3882-902. doi: 10.1002/anie.201505863. Epub 2016 Feb 2.
9
A synthesis of the C1-C15 domain of the halichondrins.海兔毒素C1-C15结构域的合成。
Tetrahedron Lett. 2008 Apr 1;49(18):2939-2941. doi: 10.1016/j.tetlet.2008.03.018.
10
Synthesis and structure assignment of the minor metabolite arising from the frog pathogen Mycobacterium liflandii.青蛙病原体利夫兰分枝杆菌产生的次要代谢产物的合成与结构确定
Tetrahedron Lett. 2010 Mar 31;51(13):1782-1785. doi: 10.1016/j.tetlet.2010.01.105.

本文引用的文献

1
Comparison of the activities of the truncated halichondrin B analog NSC 707389 (E7389) with those of the parent compound and a proposed binding site on tubulin.截短型海兔毒素B类似物NSC 707389（E7389）与母体化合物的活性比较以及其在微管蛋白上的假定结合位点。
Mol Pharmacol. 2006 Dec;70(6):1866-75. doi: 10.1124/mol.106.026641. Epub 2006 Aug 29.
2
Halichondrin B: synthesis of the C1-C22 subunit.海兔毒素B：C1-C22亚基的合成
J Org Chem. 2005 Nov 11;70(23):9382-98. doi: 10.1021/jo051479m.
3
Catalytic Ni/Cr-mediated macrocyclization without use of high-dilution techniques.无需使用高稀释技术的催化镍/铬介导的大环化反应。
J Am Chem Soc. 2005 Nov 9;127(44):15382-3. doi: 10.1021/ja055966v.
4
The primary antimitotic mechanism of action of the synthetic halichondrin E7389 is suppression of microtubule growth.合成海兔毒素E7389的主要抗有丝分裂作用机制是抑制微管生长。
Mol Cancer Ther. 2005 Jul;4(7):1086-95. doi: 10.1158/1535-7163.MCT-04-0345.
5
Macrocyclic ketone analogues of halichondrin B.海兔毒素B的大环酮类似物
Bioorg Med Chem Lett. 2004 Nov 15;14(22):5551-4. doi: 10.1016/j.bmcl.2004.08.069.
6
A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B.一种用于构建海兔毒素B的C8-C14多环环系的简单但极其有效的装置。
J Am Chem Soc. 2004 Jun 30;126(25):7770-1. doi: 10.1021/ja047826b.
7
A mixed resin bed for the quenching and purification of tetrabutylammonium fluoride mediated desilylating reactions.用于淬灭和纯化四丁基氟化铵介导的脱硅反应的混合树脂床。
Bioorg Med Chem Lett. 1998 Sep 8;8(17):2391-4. doi: 10.1016/s0960-894x(98)00432-6.
8
Interaction of halichondrin B and homohalichondrin B with bovine brain tubulin.海兔毒素B和高海兔毒素B与牛脑微管蛋白的相互作用。
Biochem Pharmacol. 1993 Jan 26;45(2):421-7. doi: 10.1016/0006-2952(93)90079-c.
9
Isolation and structure of the cell growth inhibitory constituents from the western Pacific marine sponge Axinella sp.
J Med Chem. 1991 Nov;34(11):3339-40. doi: 10.1021/jm00115a027.
10
Halichondrin B and homohalichondrin B, marine natural products binding in the vinca domain of tubulin. Discovery of tubulin-based mechanism of action by analysis of differential cytotoxicity data.海兔毒素B和高海兔毒素B，这两种海洋天然产物可与微管蛋白的长春花结构域结合。通过分析差异细胞毒性数据发现基于微管蛋白的作用机制。
J Biol Chem. 1991 Aug 25;266(24):15882-9.