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

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.

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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。

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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

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