ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate | 671789-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate
• 英文别名: ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-morpholino-β-L-ido-heptofuran]uronate；ethyl (3S)-3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-morpholin-4-ylpropanoate
• CAS: 671789-38-1
• 化学式: C₂₃H₃₃NO₇
• 分子量: 435.518
• InChiKey: MUQUCWJZUXXCBG-AOIWZFSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 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 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate 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3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-morpholino-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：

  3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 以 乙醇 、 甲苯 为溶剂， 生成 ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(morpholin-4-yl)-β-L-ido-heptofuranuronate
  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