Mild and Chemoselective Triethylsilane-Mediated Debenzylation for Phosphate Synthesis

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-24 DOI:10.1021/acs.orglett.4c04258
Luke E. Hodson, Paul Joseph Tholath, Leon Jacobs, Nicole Pribut, Gouthami Pashikanti, Aletta E. van der Westhuyzen, David Laws, III, Dennis C. Liotta
{"title":"Mild and Chemoselective Triethylsilane-Mediated Debenzylation for Phosphate Synthesis","authors":"Luke E. Hodson, Paul Joseph Tholath, Leon Jacobs, Nicole Pribut, Gouthami Pashikanti, Aletta E. van der Westhuyzen, David Laws, III, Dennis C. Liotta","doi":"10.1021/acs.orglett.4c04258","DOIUrl":null,"url":null,"abstract":"The synthetic utility of tetrabenzyl pyrophosphate for achieving chemoselective phosphorylation of phenols, as well as primary, secondary, and tertiary alcohols, is reported here. Additionally, we introduce a rapid, mild, and chemoselective debenzylation procedure, enabling access to phosphates in the presence of redox sensitive groups. Finally, stoichiometrically controlled monodebenzylation provides a versatile platform for late-stage divergent synthesis of phosphodiester and phosphoramidate chemical libraries.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"52 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04258","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

The synthetic utility of tetrabenzyl pyrophosphate for achieving chemoselective phosphorylation of phenols, as well as primary, secondary, and tertiary alcohols, is reported here. Additionally, we introduce a rapid, mild, and chemoselective debenzylation procedure, enabling access to phosphates in the presence of redox sensitive groups. Finally, stoichiometrically controlled monodebenzylation provides a versatile platform for late-stage divergent synthesis of phosphodiester and phosphoramidate chemical libraries.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
温和和化学选择性三乙基硅烷介导的磷酸合成脱苯反应
焦磷酸四苯甲酯的合成用途,以实现苯酚的化学选择性磷酸化,以及伯、仲、叔醇,报告在这里。此外,我们还引入了一种快速、温和和化学选择性的去苯化过程,使其能够在氧化还原敏感基团存在的情况下获得磷酸盐。最后,化学计量控制的单去苄基化为磷酸二酯和磷酰胺化学文库的后期发散合成提供了一个通用的平台。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
期刊最新文献
Toward N-Linked Glycoproteins: Three-Step Synthesis of Glycan-Asparagine Conjugates from Unprotected Sugars. Expanding Isothiazole Chemical Space: Synthesis and Derivatization of [c]-Fused Saturated Rings. Access to Imidazolidin-2-ones via Azocarboxamide-Enabled Enantioselective 1,2-Diamination of Aldehyde. A Novel Heat-Resistant Energetic Material: Pyrazolopyrimidine-Bistetrazole Compound. Chirality in Abundance: A Reagent-Controlled Access to Multiple Stereoisomers of Functionalized Bishomocubanes.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1