ethyl [5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-5-morpholino-β-L-ido-heptofuran]uronate | 671789-37-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl [5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-5-morpholino-β-L-ido-heptofuran]uronate
• 英文别名: ethyl 3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate；ethyl (3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-morpholin-4-ylpropanoate
• CAS: 671789-37-0
• 化学式: C₁₇H₂₉NO₇
• 分子量: 359.42
• InChiKey: WLDBFQYIVOFYHM-PJGLDBICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl [5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-5-morpholino-β-L-ido-heptofuran]uronate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以88%的产率得到5,6-dideoxy-1,2-O-isopropylidene-5-morpholino-3-O-methyl-β-L-ido-heptofuranuronic acid
  参考文献：
  名称：

  Synthesis of glycosylated β-Amino hydroxamates as new class of antimalarials

  摘要：

  Glycosylated beta-amino acids (3-18, 38, 39), obtained by hydrolysis of glycosylated beta-amino esters on reaction with hydroxylamine hydrochloride in presence of DIC/DCC afforded glycosyl beta-amino hydroxamates (19-34, 40, 41) in fair to good yields. Compounds (19-34, 40, 41) were screened against human malarial parasite Plasmodium falciparum in vitro for their schizontocidal activity. Compounds (19, 24, 26, 28, 40 and 41) exhibited good activity at 2 mug/mL concentrations. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.038
• 作为产物：
  描述：

  1,2-O-异亚丙基-3-O-甲基-Alpha-D-木五二呋喃醛糖-(1,4) 以 乙醇 、 甲苯 为溶剂， 生成 ethyl [5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-5-morpholino-β-L-ido-heptofuran]uronate
  参考文献：
  名称：

  CONJUGATE ADDITION OF AMINES TO SUGAR DERIVED OLEFINIC ESTERS: SYNTHESIS OF GLYCOSYLATED AMINO ESTERS AS DNA TOPOISOMERASE-II INHIBITORS

  摘要：

  Conjugate addition of amines to olefinic esters derived from sugars leading to formation of glycosylated amino esters in a stereoselective manner is described. Some of the synthesized compounds possess DNA topoisomerase-II enzyme inhibitory activities at low concentrations.

  DOI：

  10.1081/car-120016857

文献信息

• CONJUGATE ADDITION OF AMINES TO SUGAR DERIVED OLEFINIC ESTERS: SYNTHESIS OF GLYCOSYLATED AMINO ESTERS AS DNA TOPOISOMERASE-II INHIBITORS
  作者：A. Khan、R. Tripathi、V. Tiwari、R. Mishra、V.J. Reddy、J. Saxena

  DOI：10.1081/car-120016857

  日期：——

  Conjugate addition of amines to olefinic esters derived from sugars leading to formation of glycosylated amino esters in a stereoselective manner is described. Some of the synthesized compounds possess DNA topoisomerase-II enzyme inhibitory activities at low concentrations.
• Synthesis of glycosylated β-Amino hydroxamates as new class of antimalarials
  作者：R.C. Mishra、Renu Tripathi、Diksha Katiyar、Neetu Tewari、Deepti Singh、R.P. Tripathi

  DOI：10.1016/j.bmc.2003.09.038

  日期：2003.12

  Glycosylated beta-amino acids (3-18, 38, 39), obtained by hydrolysis of glycosylated beta-amino esters on reaction with hydroxylamine hydrochloride in presence of DIC/DCC afforded glycosyl beta-amino hydroxamates (19-34, 40, 41) in fair to good yields. Compounds (19-34, 40, 41) were screened against human malarial parasite Plasmodium falciparum in vitro for their schizontocidal activity. Compounds (19, 24, 26, 28, 40 and 41) exhibited good activity at 2 mug/mL concentrations. (C) 2003 Elsevier Ltd. All rights reserved.