• 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

一种直截了当的二苯甲基保护方法及一些嘧啶核苷的脱保护。

A straightforward diphenylmethyl protection method and deprotection of some pyrimidine nucleosides.

机构信息

Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, Leuven 3000, Belgium.

出版信息

Molecules. 2013 Jul 18;18(7):8524-34. doi: 10.3390/molecules18078524.

DOI:10.3390/molecules18078524
PMID:23873390
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6270414/
Abstract

Benzhydryl protection of primary and secondary alcohols has been reported previously via reaction with metal alcoholates. Our aim was to find generally useful and very mild conditions for the alcoholic protection and deprotection of nucleosides with the diphenylmethyl group. This was accomplished for some pyrimidine nucleosides using PdCl₂ as the transition metal catalyst, and with optimization yields of 70-90% have been achieved. A lack of solubility of other nucleosides hampers its more general use.

摘要

先前已有文献报道,通过与金属醇盐反应,可以实现伯醇和仲醇的苄基保护。我们的目的是找到一种普遍适用且非常温和的条件,用于用二苯甲基保护和脱保护核苷。使用 PdCl₂作为过渡金属催化剂,已经实现了一些嘧啶核苷的这一转化,优化后的产率为 70-90%。其他核苷的溶解度问题限制了其更广泛的应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4a3/6270414/d75c86a8e88e/molecules-18-08524-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4a3/6270414/844364bb8743/molecules-18-08524-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4a3/6270414/35636017e800/molecules-18-08524-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4a3/6270414/d75c86a8e88e/molecules-18-08524-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4a3/6270414/844364bb8743/molecules-18-08524-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4a3/6270414/35636017e800/molecules-18-08524-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4a3/6270414/d75c86a8e88e/molecules-18-08524-g003.jpg

相似文献

1
A straightforward diphenylmethyl protection method and deprotection of some pyrimidine nucleosides.一种直截了当的二苯甲基保护方法及一些嘧啶核苷的脱保护。
Molecules. 2013 Jul 18;18(7):8524-34. doi: 10.3390/molecules18078524.
2
Propargyl 1,2-orthoesters for a catalytic and stereoselective synthesis of pyrimidine nucleosides.用于催化立体选择性合成嘧啶核苷的炔丙基1,2-原酸酯
J Org Chem. 2015 Feb 6;80(3):1499-505. doi: 10.1021/jo502413z. Epub 2015 Jan 8.
3
7-substituted 8-aza-7-deazapurines and 2,8-diaza-7-deaza-purines: synthesis of nucleosides and oligonucleotides.7-取代的8-氮杂-7-脱氮嘌呤和2,8-二氮杂-7-脱氮嘌呤:核苷和寡核苷酸的合成
Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):869-73. doi: 10.1081/ncn-200059218.
4
Chemoselective benzylation of unprotected anthranilic acids with benzhydryl alcohols by water-soluble Au(III)/TPPMS in water.水溶性 Au(III)/TPPMS 体系水相中对未保护的邻氨基苯甲酸的苄基化反应的选择性研究。
J Org Chem. 2013 Jul 5;78(13):6714-20. doi: 10.1021/jo401064f. Epub 2013 Jun 18.
5
Palladium catalysts for aerobic oxidative kinetic resolution of secondary alcohols based on mechanistic insight.基于机理洞察的用于仲醇有氧氧化动力学拆分的钯催化剂
Org Lett. 2003 Jan 9;5(1):63-5. doi: 10.1021/ol027190y.
6
A one step synthetic approach to L-pyrimidine nucleosides using natural phosphate coated with potassium iodide as catalyst.一种以碘化钾包覆的天然磷酸盐为催化剂一步合成L-嘧啶核苷的方法。
Nucleic Acids Symp Ser (Oxf). 2008(52):549-50. doi: 10.1093/nass/nrn278.
7
Palladium-mediated C5 substitution of pyrimidine nucleosides.钯介导的嘧啶核苷的C5取代反应。
Curr Protoc Nucleic Acid Chem. 2001 May;Chapter 1:Unit 1.1. doi: 10.1002/0471142700.nc0101s00.
8
A simple and efficient synthesis of puromycin, 2,2'-anhydro-pyrimidine nucleosides, cytidines and 2',3'-anhydroadenosine from 3',5'-O-sulfinyl xylo-nucleosides.一种从3',5'-O-亚磺酰木糖核苷简单高效合成嘌呤霉素、2,2'-脱水嘧啶核苷、胞苷和2',3'-脱水腺苷的方法。
Nucleosides Nucleotides Nucleic Acids. 2006;25(7):719-34. doi: 10.1080/15257770600725929.
9
Rhodium-catalyzed reductive modification of pyrimidine nucleosides, nucleotide phosphates, and sugar nucleotides.铑催化的嘧啶核苷、核苷酸磷酸酯和糖核苷酸的还原修饰。
Carbohydr Res. 2020 Feb;488:107893. doi: 10.1016/j.carres.2019.107893. Epub 2019 Dec 19.
10
New Catalytic Asymmetric Formation of Oxygen Heterocycles Bearing Nucleoside Bases at the Anomeric Carbon.新型手性催化的含核苷碱基的氧杂环在非端碳上的形成。
J Am Chem Soc. 2019 Jul 3;141(26):10199-10204. doi: 10.1021/jacs.9b06050. Epub 2019 Jun 17.

引用本文的文献

1
Titanium tetrafluoride catalysis for the dehydrative conversion of diphenylmethanols to symmetric and unsymmetric ethers.四氟化钛催化二苯甲醇脱水转化为对称和不对称醚。
RSC Adv. 2024 Aug 2;14(33):24236-24239. doi: 10.1039/d4ra04712e. eCollection 2024 Jul 26.
2
A Convenient Protecting Group for Uridine Ureido Nitrogen: (4,4'-Bisfluorophenyl)methoxymethyl group.尿苷脲基氮的一种便捷保护基团:(4,4'-双氟苯基)甲氧基甲基基团。
Synthesis (Stuttg). 2021 Aug;53(15):2643-2650. doi: 10.1055/a-1464-2473. Epub 2021 Mar 25.
3
Formation of DPM ethers using O-diphenylmethyl trichloroacetimidate under thermal conditions.

本文引用的文献

1
Glycosylation studies on conformationally restricted 3,5-O-(di-tert-butylsilylene)-D-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-D-galactofuranosylation.对构象受限的 3,5-O-(二叔丁基二硅基烯基)-D-半乳糖呋喃糖基三氯乙酰亚胺供体进行糖基化研究,用于 1,2-顺式 α-D-半乳糖呋喃糖基化。
Carbohydr Res. 2011 Dec 27;346(18):2838-48. doi: 10.1016/j.carres.2011.10.004. Epub 2011 Oct 12.
2
A preparation of N-Fmoc-N-methyl-alpha-amino acids and N-nosyl-N-methyl-alpha-amino acids.N-Fmoc-N-甲基-α-氨基酸和 N-硝酰基-N-甲基-α-氨基酸的混合物。
Amino Acids. 2010 Jan;38(1):133-43. doi: 10.1007/s00726-008-0221-8. Epub 2008 Dec 3.
3
在热条件下使用O-二苯甲基三氯乙酰亚胺酯形成DPM醚。
Org Biomol Chem. 2016 Feb 7;14(5):1623-8. doi: 10.1039/c5ob02455b.
Protecting groups for RNA synthesis: an increasing need for selective preparative methods.
用于RNA合成的保护基团:对选择性制备方法的需求日益增加。
Chem Soc Rev. 2008 Dec;37(12):2668-75. doi: 10.1039/b809851d. Epub 2008 Oct 3.
4
Direct carbon-carbon bond formation from alcohols and active methylenes, alkoxyketones, or indoles catalyzed by indium trichloride.三氯化铟催化醇与活性亚甲基、烷氧基酮或吲哚直接形成碳-碳键。
Angew Chem Int Ed Engl. 2006 Jan 23;45(5):793-6. doi: 10.1002/anie.200503263.
5
Secondary benzylation using benzyl alcohols catalyzed by lanthanoid, scandium, and hafnium triflate.使用镧系元素、钪和三氟甲磺酸铪催化苄醇进行二次苄基化反应。
J Org Chem. 2003 Nov 28;68(24):9340-7. doi: 10.1021/jo034255h.