ethyl 3-O-methyl-5-(benzylamino)-5,6-dideoxy-1,2-O-isopropylideneheptofuranuronate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-O-methyl-5-(benzylamino)-5,6-dideoxy-1,2-O-isopropylideneheptofuranuronate
• 英文别名: ethyl [3-O-methyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene]-heptofuranuronate；ethyl 3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-(benzylamino)propanoate
• 化学式: C₂₀H₂₉NO₆
• 分子量: 379.453
• InChiKey: LWSUYTSBYPLYDM-MSEHENTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 ethyl 3-O-methyl-5-(benzylamino)-5,6-dideoxy-1,2-O-isopropylideneheptofuranuronate 在 硫酸 、 溶剂黄146 作用下， 生成 ethyl [1,2-di-O-acetyl-5-benzylamino-5,6-dideoxy-3-O-methyl]-α-D-xylo-hepto-1,4-furanuronate 、 ethyl [1,2-di-O-acetyl-5-benzylamino-5,6-dideoxy-3-O-methyl]-β-D-xylo-hepto-1,4-furanuronate
  参考文献：
  名称：

  Synthesis and DNA Topoisomerase-II Inhibitory Activity of Unnatural Nucleosides

  摘要：

  The synthesis and biological activities Of a number of unnatural nucleosides (23 - 43) is described. Nucleosides have been synthesized by SnCl4-catalyzed condensation of amino sugar acetates and silylated modified pyrimidines. Few of the 2'-O-acetyl derivatives of the nucleosides were hydrolyzed to the respective hydroxy derivatives 0 treatment with methanol saturated with ammonia. The compounds were screened against Filarial DNA-topoisomerase-II but on one of the compounds (29) inhibited this enzyme at 40 mug/mL of reaction mixture.

  DOI：

  10.1081/ncn-200046776
• 作为产物：
  描述：

  (E)-ethyl-(3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene)-α-D-1,4-heptofuranosyl-5-enoate 、 苄胺 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以75%的产率得到ethyl 3-O-methyl-5-(benzylamino)-5,6-dideoxy-1,2-O-isopropylideneheptofuranuronate
  参考文献：
  名称：

  Tetra-n-butylammonium fluoride: an efficient base for aza-Michael addition—synthesis of glycosyl β-amino acid esters

  摘要：

  A mild and efficient route to glycosyl beta-amino acid esters. exploiting the stereoselective Michael addition of benzylamine, in the presence of tetra-n-butylammonium fluoride, to sugar derived gamma-alkoxy alpha,beta-unsaturated esters is described. (C) 2602 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00047-2