海胆的萘醌类色素。原乙酸三甲酯作为一种有效的试剂，用于对尖晶石色素、尖晶石色素 D 和 E 以及回声色素 A 的 β-OH 基团进行 O-甲基化反应

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Russian Chemical Bulletin Pub Date : 2024-08-31 DOI:10.1007/s11172-024-4328-1

O. P. Shestak, N. N. Balaneva, V. L. Novikov, V. P. Glazunov

{"title":"海胆的萘醌类色素。原乙酸三甲酯作为一种有效的试剂，用于对尖晶石色素、尖晶石色素 D 和 E 以及回声色素 A 的 β-OH 基团进行 O-甲基化反应","authors":"O. P. Shestak, N. N. Balaneva, V. L. Novikov, V. P. Glazunov","doi":"10.1007/s11172-024-4328-1","DOIUrl":null,"url":null,"abstract":"<div><p>Trimethyl orthoacetate (MeC(OMe)<sub>3</sub>, TMOA) is a convenient reagent for both selective and complete O-methylation of the β-OH groups of sea urchin pigments such as spinazarin, spinochromes D and E, and echinochrome A. The reactions of these compounds with TMOA make it possible to furnish preparative amounts of 6-monomethyl ethers of spinochrome D and echinochrome A, 7-monomethyl ether (namakochrome) and 6,7-dimethyl ether of spinochrome E, which are difficult to prepare by other methods, and to carry out complete O-methylation of all discussed pigments. Among the known O-methylating agents, TMOA is most suitable for the preparative syntheses of methyl ethers of polyhydroxynaphthazarins.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"2082 - 2098"},"PeriodicalIF":1.7000,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Naphthoquinoid pigments of sea urchins. Trimethyl orthoacetate as an effective reagent for O-methylation of β-OH groups of spinazarin, spinochromes D and E, and echinochrome A\",\"authors\":\"O. P. Shestak, N. N. Balaneva, V. L. Novikov, V. P. Glazunov\",\"doi\":\"10.1007/s11172-024-4328-1\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Trimethyl orthoacetate (MeC(OMe)<sub>3</sub>, TMOA) is a convenient reagent for both selective and complete O-methylation of the β-OH groups of sea urchin pigments such as spinazarin, spinochromes D and E, and echinochrome A. The reactions of these compounds with TMOA make it possible to furnish preparative amounts of 6-monomethyl ethers of spinochrome D and echinochrome A, 7-monomethyl ether (namakochrome) and 6,7-dimethyl ether of spinochrome E, which are difficult to prepare by other methods, and to carry out complete O-methylation of all discussed pigments. Among the known O-methylating agents, TMOA is most suitable for the preparative syntheses of methyl ethers of polyhydroxynaphthazarins.</p></div>\",\"PeriodicalId\":756,\"journal\":{\"name\":\"Russian Chemical Bulletin\",\"volume\":\"73 7\",\"pages\":\"2082 - 2098\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2024-08-31\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Chemical Bulletin\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s11172-024-4328-1\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Chemical Bulletin","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11172-024-4328-1","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

原乙酸三甲酯（MeC(OMe)3, TMOA）是一种方便的试剂，可用于选择性地完全 O-甲基化海胆色素（如菠菜素、棘色素 D 和 E 以及回声色素 A）的 β-OH 基团。通过这些化合物与 TMOA 的反应，可以制备出用其他方法难以制备的尖晶石色素 D 和棘晶石色素 A 的 6-单甲基醚、7-单甲基醚（namakochrome）和尖晶石色素 E 的 6,7-二甲基醚，并对所有讨论过的色素进行完全的 O-甲基化反应。在已知的 O-甲基化剂中，TMOA 最适合用于制备多羟基萘酞菁甲基醚的合成。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

Naphthoquinoid pigments of sea urchins. Trimethyl orthoacetate as an effective reagent for O-methylation of β-OH groups of spinazarin, spinochromes D and E, and echinochrome A

Trimethyl orthoacetate (MeC(OMe)₃, TMOA) is a convenient reagent for both selective and complete O-methylation of the β-OH groups of sea urchin pigments such as spinazarin, spinochromes D and E, and echinochrome A. The reactions of these compounds with TMOA make it possible to furnish preparative amounts of 6-monomethyl ethers of spinochrome D and echinochrome A, 7-monomethyl ether (namakochrome) and 6,7-dimethyl ether of spinochrome E, which are difficult to prepare by other methods, and to carry out complete O-methylation of all discussed pigments. Among the known O-methylating agents, TMOA is most suitable for the preparative syntheses of methyl ethers of polyhydroxynaphthazarins.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.