(1S,2R,8R,8aR)-8-benzyloxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one | 159701-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1S,2R,8R,8aR)-8-benzyloxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one
• 英文别名: (3aR,9R,9aR,9bS)-9-benzyloxy-2,2-dimethylhexahydro-[1,3]dioxolo[4,5-a]indolizin-6(9bH)-one；(3aR,9R,9aR,9bS)-2,2-dimethyl-9-phenylmethoxy-4,7,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-a]indolizin-6-one
• CAS: 159701-87-8
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: PLJKHUCAXBQWRN-MUIFIZLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,8R,8aR)-8-benzyloxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one 在 palladium hydroxide - carbon dimethyl sulfide borane 、 氢气 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 25.0~65.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 1,2-异亚丙基苦马豆素
  参考文献：
  名称：

  Honda, Toshio; Hoshi, Michiyasu; Kanai, Kazuo, Journal of the Chemical Society. Perkin transactions I, 1994, # 15, p. 2091 - 2102

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>cyclopentanol 在 4-二甲氨基吡啶 、 氯化亚砜 、 四丙基高钌酸铵 、 4 A molecular sieve 、 盐酸羟胺 、 四丁基氟化铵 、 potassium carbonate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 (1S,2R,8R,8aR)-8-benzyloxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one
  参考文献：
  名称：

  Honda, Toshio; Hoshi, Michiyasu; Kanai, Kazuo, Journal of the Chemical Society. Perkin transactions I, 1994, # 15, p. 2091 - 2102

  摘要：

  DOI：

文献信息

• Fleetamine (3-O-α-d-glucopyranosyl-swainsonine): the synthesis of a hypothetical inhibitor of endo-α-mannosidase
  作者：Tim Quach、Sammi Tsegay、Andrew J. Thompson、Nikolay V. Kukushkin、Dominic S. Alonzi、Terry D. Butters、Gideon J. Davies、Spencer J. Williams

  DOI：10.1016/j.tetasy.2012.06.011

  日期：2012.7

  3-O-alpha-D-Glucopyranosyl-swainsonine was originally proposed(17) as a potential inhibitor of the mammalian enzyme endo-alpha-mannosidase, but its synthesis has not been reported. Herein we report the total synthesis of this enigmatic compound, utilizing a halide-ion catalysed glycosylation of a swainsonine lactam with a glucosyl iodide donor as the key step. The resulting inhibitor was evaluated as an inhibitor of human endo-alpha-mannosidase, and as a ligand for bacterial orthologs from Bacteroides thetaiotaomicron and Bacteroides xylanisolvens, including active-centre variants, although no evidence for binding or inhibition was observed. The surprising lack of binding was rationalized by using structural alignment with an endo-alpha-mannosidase inhibitor complex, which identified deleterious interactions with the swainsonine piperidine ring and an essential active site residue. (C) 2012 Elsevier Ltd. All rights reserved.