(3R,4R,5R)-3,4-dihydroxy-5-(2-hydroxyethyl)-N-methylpiperidine hydrochloride | 1338213-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4R,5R)-3,4-dihydroxy-5-(2-hydroxyethyl)-N-methylpiperidine hydrochloride
• 英文别名: N-methyl-5-epi-homoisofagomine hydrochloride；(3R,4R,5R)-5-(2-hydroxyethyl)-1-methylpiperidine-3,4-diol;hydrochloride
• CAS: 1338213-08-3
• 化学式: C₈H₁₇NO₃*ClH
• 分子量: 211.689
• InChiKey: IMBUTHRIYOKGDK-QTPPMTSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.93
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 在 palladium 10% on activated carbon 、 氢气 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 25.0~30.0 ℃ 、551.59 kPa 条件下， 反应 44.0h， 以0.038 g的产率得到(3R,4R,5R)-3,4-dihydroxy-5-(2-hydroxyethyl)-N-methylpiperidine hydrochloride
  参考文献：
  名称：

  Synthesis of new six- and seven-membered 1-N-iminosugars as promising glycosidase inhibitors

  摘要：

  New six- and seven-membered 1-N-iminosugars were prepared from D-glucose by the stereoselective Michael addition of nitromethane to D-glucose derived alpha,beta-unsaturated ester A followed by one pot reduction of nitro/ester functionality and subsequent amine protection to get N-Cbz protected aminol 6. Hydrolysis of 1,2-acetonide and reductive aminocyclization gave seven membered 1-N-iminosugar 5b. While, hydrolysis of 1,2-acetonide followed by NaIO(4) oxidative cleavage and hydrogenation using 10% Pd(OH)(2)/C, H(2) gave six membered 1-N-iminosugar 4a; the hydrogenation using 10% Pd/C-H(2) however, gave N-methyl substituted 1-N-iminosugar 4b. The hydrochloride salts of 4a/4b and 5b were found to be specific alpha-galactosidase and moderate alpha-glucosidae inhibitors, respectively, in micro molar range. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.059

文献信息

• Synthesis of new six- and seven-membered 1-N-iminosugars as promising glycosidase inhibitors
  作者：Amit M. Jabgunde、Navnath B. Kalamkar、Sanjay T. Chavan、Sushma G. Sabharwal、Dilip D. Dhavale

  DOI：10.1016/j.bmc.2011.07.059

  日期：2011.10

  New six- and seven-membered 1-N-iminosugars were prepared from D-glucose by the stereoselective Michael addition of nitromethane to D-glucose derived alpha,beta-unsaturated ester A followed by one pot reduction of nitro/ester functionality and subsequent amine protection to get N-Cbz protected aminol 6. Hydrolysis of 1,2-acetonide and reductive aminocyclization gave seven membered 1-N-iminosugar 5b. While, hydrolysis of 1,2-acetonide followed by NaIO(4) oxidative cleavage and hydrogenation using 10% Pd(OH)(2)/C, H(2) gave six membered 1-N-iminosugar 4a; the hydrogenation using 10% Pd/C-H(2) however, gave N-methyl substituted 1-N-iminosugar 4b. The hydrochloride salts of 4a/4b and 5b were found to be specific alpha-galactosidase and moderate alpha-glucosidae inhibitors, respectively, in micro molar range. (C) 2011 Elsevier Ltd. All rights reserved.