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

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

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引用次数: 5

摘要

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。

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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

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.

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来源期刊

Chemical & pharmaceutical bulletin 医学-化学综合

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.