Ce(OTf)3催化合成吡喃葡萄糖醛酸-6,1-内酯：获得阿瑞司他丁 A 肽片段糖苷共轭物的关键中间体

IF 0.7 4区化学 Q4 CHEMISTRY, ORGANIC

Letters in Organic Chemistry Pub Date : 2024-08-28 DOI:10.2174/0115701786325021240817182955

A. Mezrai, L. Mrah, Z. Khiati, A. Keniche

{"title":"Ce(OTf)3催化合成吡喃葡萄糖醛酸-6,1-内酯：获得阿瑞司他丁 A 肽片段糖苷共轭物的关键中间体","authors":"A. Mezrai, L. Mrah, Z. Khiati, A. Keniche","doi":"10.2174/0115701786325021240817182955","DOIUrl":null,"url":null,"abstract":"In this work, 2,3,4-tri-O-acetyl-D-glucurono-6,1-lactone has been prepared from glucuronic acid in two steps by converting it into glucuronic anhydride. In the presence of a catalytic amount of Ce(OTf)3 (10 examples) in ethyl acetate, the glucuronic anhydride provided 6.1-lactone in good to excellent yields. This lactone was used to prepare the novel glycoconjugates of peptidic fragments of arenastatin A, a sponge cytotoxic depsipeptide, and its analogues.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"27 1","pages":""},"PeriodicalIF":0.7000,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Ce(OTf)3-Catalyzed Synthesis of Glucopyranurono-6,1-Lactone: A Key Intermediate for Obtaining Glycoconjugates of Peptidic Fragments of Arenastatin A\",\"authors\":\"A. Mezrai, L. Mrah, Z. Khiati, A. Keniche\",\"doi\":\"10.2174/0115701786325021240817182955\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"In this work, 2,3,4-tri-O-acetyl-D-glucurono-6,1-lactone has been prepared from glucuronic acid in two steps by converting it into glucuronic anhydride. In the presence of a catalytic amount of Ce(OTf)3 (10 examples) in ethyl acetate, the glucuronic anhydride provided 6.1-lactone in good to excellent yields. This lactone was used to prepare the novel glycoconjugates of peptidic fragments of arenastatin A, a sponge cytotoxic depsipeptide, and its analogues.\",\"PeriodicalId\":18116,\"journal\":{\"name\":\"Letters in Organic Chemistry\",\"volume\":\"27 1\",\"pages\":\"\"},\"PeriodicalIF\":0.7000,\"publicationDate\":\"2024-08-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Letters in Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.2174/0115701786325021240817182955\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Letters in Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.2174/0115701786325021240817182955","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

在这项工作中，通过将葡萄糖醛酸转化为葡萄糖醛酸酐，分两步从葡萄糖醛酸制备出了 2,3,4-三-O-乙酰基-D-葡萄糖醛酸-6,1-内酯。在乙酸乙酯中存在催化量的 Ce（OTf）3（10 例）的情况下，葡萄糖醛酸酐以良好至极好的收率提供了 6.1-内酯。这种内酯被用来制备新型的阿那斯丁 A（一种海绵细胞毒性去肽类化合物）肽片段糖共轭物及其类似物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Ce(OTf)3-Catalyzed Synthesis of Glucopyranurono-6,1-Lactone: A Key Intermediate for Obtaining Glycoconjugates of Peptidic Fragments of Arenastatin A

In this work, 2,3,4-tri-O-acetyl-D-glucurono-6,1-lactone has been prepared from glucuronic acid in two steps by converting it into glucuronic anhydride. In the presence of a catalytic amount of Ce(OTf)3 (10 examples) in ethyl acetate, the glucuronic anhydride provided 6.1-lactone in good to excellent yields. This lactone was used to prepare the novel glycoconjugates of peptidic fragments of arenastatin A, a sponge cytotoxic depsipeptide, and its analogues.

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

Letters in Organic Chemistry 化学-有机化学

CiteScore

1.30

自引率

12.50%

发文量

135

审稿时长

7 months

期刊介绍： Aims & Scope Letters in Organic Chemistry publishes original letters (short articles), research articles, mini-reviews and thematic issues based on mini-reviews and short articles, in all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is to publish quality papers rapidly by taking full advantage of latest technology for both submission and review of the manuscripts. The journal is an essential reading for all organic chemists belonging to both academia and industry.