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Synthesis of glucosamine vinyl ether derivative and its deuterated analog
Russian Chemical Bulletin ( IF 1.7 ) Pub Date : 2020-07-01 , DOI: 10.1007/s11172-020-2915-3
K. S. Rodygin , V. V. Voronin , M. S. Ledovskaya

The use of calcium carbide (in the presence of H2O) as a source of acetylene in the reaction with methyl 2-amino-4,6-O-benzylidene-2-deoxy-β-d-glucopyranoside under superbasic conditions (KF, KOH, DMSO, 130 °C, 3 h) led to the corresponding vinyl ether in 78% yield. The vinylation does not affect other reaction centers. Replacement of water with deuterium oxide in the reaction mixture gave a stable deuterated analog of this vinyl ether in 72% yield. The one-step isotopic enrichment was practically quantitative (isotopic purity >96%). Introduced deuterium atoms can be used as a convenient label in further transformations.

中文翻译:

氨基葡萄糖乙烯基醚衍生物及其氘代类似物的合成

在超碱性条件(KF、KOH)下使用碳化钙(在 H2O 存在下)作为乙炔来源与甲基 2-氨基-4,6-O-苄叉-2-脱氧-β-d-吡喃葡萄糖苷反应, DMSO, 130 °C, 3 h) 产生相应的乙烯基醚,产率为 78%。乙烯基化不影响其他反应中心。在反应混合物中用氧化氘代替水得到稳定的这种乙烯基醚的氘代类似物,产率为 72%。一步同位素富集实际上是定量的(同位素纯度 > 96%)。引入的氘原子可用作进一步转化中的方便标记。
更新日期:2020-07-01
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