(1S,2R,8R,8aR)-2,8-bis(acetoxy)-1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)octahydroindolizine | 1393529-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,8R,8aR)-2,8-bis(acetoxy)-1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)octahydroindolizine
• CAS: 1393529-15-1
• 化学式: C₂₆H₃₇NO₁₄
• 分子量: 587.578
• InChiKey: YUKCXITUKZFKEC-JVZXMRAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  179.5
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,8R,8aR)-2,8-bis(acetoxy)-1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)octahydroindolizine 在 sodium methylate 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以5.5 mg的产率得到(1S,2R,8R,8aR)-2,8-bis(hydroxy)-1-(α-D-glucopyranosyloxy)-octahydroindolizine hydrochloride
  参考文献：
  名称：

  Fleetamine (3-O-α-d-glucopyranosyl-swainsonine): the synthesis of a hypothetical inhibitor of endo-α-mannosidase

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2012.06.011
• 作为产物：
  描述：

  (1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one 在 吡啶 、 dimethyl sulfide borane 、 20 % Pd(OH)2/C 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 55.0 ℃ 、482.64 kPa 条件下， 反应 199.5h， 生成 (1S,2R,8R,8aR)-2,8-bis(acetoxy)-1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)octahydroindolizine
  参考文献：
  名称：

  Fleetamine (3-O-α-d-glucopyranosyl-swainsonine): the synthesis of a hypothetical inhibitor of endo-α-mannosidase

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2012.06.011