唾液酸的研究。十八:3-脱氧-d -甘油-d -半乳糖-2-非磺酰吡喃酸芳基-α-糖苷的合成

IF 1.5 4区医学 Q4 CHEMISTRY, MEDICINAL

Chemical & pharmaceutical bulletin Pub Date : 1989-03-25 DOI:10.1248/CPB.37.821

Mitsunobu Nakamura, K. Furuhata, H. Ogura

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引用次数: 11

摘要

在Williamson反应条件下，苯氧化钠、对硝基苯氧化钠和4-甲基伞草酸钠与苯(4,5,7,8,9 -五- o-乙酰-3-脱氧-d -甘油-β- d -半乳糖-2-非磺酰吡喃基氯)酸酯缩合得到相应的α-糖苷，收率较高。这些α-糖苷的脱保护反应得到3-脱氧-d -甘油-d -半乳糖-2-壬磺吡喃酸(KDN)的苯基、对硝基苯基和4-甲基伞形膦基α-糖苷钠盐。通过质子核磁共振(1H-NMR)和圆二色性(CD)光谱分析对糖基化产物的结构和立体化学性质进行了表征。

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Studies on sialic acids. XVIII: Synthesis of aryl-α-glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (KDN)

Condensation of sodium phenoxide, sodium p-nitrophenoxide, and sodium 4-methylumbelliferonate with benzyl (4, 5, 7, 8, 9-penta-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosyl chlorid)onate under the Williamson reaction conditions gave the corresponding α-glycosides in good yields. Deprotection reaction of these α-glycosides gave sodium salts of phenyl-, p-nitrophenyl-, and 4-methylumbelliferonyl-α-glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (KDN). The structure and stereochemistry of the glycosylation products were determined by proton nuclear magnetic resonance (1H-NMR) and circular dichroism (CD) 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.