Synthesis of α-N-Glycosides of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) Using Nucleobases and Their Photocycloaddition to 2, 3-Dimethyl-2-butene

IF 1.5 4区 医学 Q4 CHEMISTRY, MEDICINAL Chemical & pharmaceutical bulletin Pub Date : 1994-11-15 DOI:10.1248/CPB.42.2352
Xue-Long Sun, N. Haga, H. Ogura, H. Takayanagi
{"title":"Synthesis of α-N-Glycosides of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) Using Nucleobases and Their Photocycloaddition to 2, 3-Dimethyl-2-butene","authors":"Xue-Long Sun, N. Haga, H. Ogura, H. Takayanagi","doi":"10.1248/CPB.42.2352","DOIUrl":null,"url":null,"abstract":"α-N-Glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) having a nucleobase, such as uracil, thymine, 5-fluorouracil or cytosine, were synthesized. Their acetone-sensitized photocycloaddition to 2, 3-dimethyl-2-butene under near-UV irradiation gave a pair of diastereomers having a cyclobutane ring. The absolute configuration of the bridgehead carbon atoms in the products was identified by measurement of specific rotation as well as 1H-NMR spectral analysis.","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"46 1","pages":"2352-2356"},"PeriodicalIF":1.5000,"publicationDate":"1994-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"5","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical & pharmaceutical bulletin","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1248/CPB.42.2352","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 5

Abstract

α-N-Glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) having a nucleobase, such as uracil, thymine, 5-fluorouracil or cytosine, were synthesized. Their acetone-sensitized photocycloaddition to 2, 3-dimethyl-2-butene under near-UV irradiation gave a pair of diastereomers having a cyclobutane ring. The absolute configuration of the bridgehead carbon atoms in the products was identified by measurement of specific rotation as well as 1H-NMR spectral analysis.
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
核碱基合成3-脱氧- d -甘油- d -半乳糖-2-非醛酸(KDN) α- n -糖苷及其与2,3 -二甲基-2-丁烯的光环加成
合成了具有核碱基的3-脱氧-d -甘油-d -半乳糖-2-非醛酸(KDN)的α- n -糖苷,如尿嘧啶、胸腺嘧啶、5-氟尿嘧啶或胞嘧啶。它们的丙酮敏化光环在近紫外照射下与2,3 -二甲基-2-丁烯加成,得到一对具有环丁烷环的非对映体。通过比旋测量和1H-NMR谱分析,确定了产物中桥头堡碳原子的绝对构型。
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
CiteScore
3.20
自引率
5.90%
发文量
132
审稿时长
1.7 months
期刊介绍: The CPB covers various chemical topics in the pharmaceutical and health sciences fields dealing with biologically active compounds, natural products, and medicines, while BPB deals with a wide range of biological topics in the pharmaceutical and health sciences fields including scientific research from basic to clinical studies. For details of their respective scopes, please refer to the submission topic categories below. Topics: Organic chemistry In silico science Inorganic chemistry Pharmacognosy Health statistics Forensic science Biochemistry Pharmacology Pharmaceutical care and science Medicinal chemistry Analytical chemistry Physical pharmacy Natural product chemistry Toxicology Environmental science Molecular and cellular biology Biopharmacy and pharmacokinetics Pharmaceutical education Chemical biology Physical chemistry Pharmaceutical engineering Epidemiology Hygiene Regulatory science Immunology and microbiology Clinical pharmacy Miscellaneous.
期刊最新文献
Synthetic Studies on Vitamin D Derivatives with Diverse but Selective Biological Activities. Theoretical Framework for Novel Catalytic Biomolecules Composed of Multiple Peptides Two Preparation Methods for Peptide Thioester Containing Tyr(SO3H) Residue(s) without the Use of Protecting Group for Sulfate Moiety Total Synthesis of Dinorsesquiterpenoid Oxyphyllin A/Belchinoid A Evaluation of STAT3 Inhibition by Cancer Chemopreventive Trichothecenes Derived from Metabolites of Trichothecium roseum
×
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:481959085
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