(2R,3R,4R,5S)-2-ethylpiperidine-3,4,5-triol | 1000855-29-7

• 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: (2R,3R,4R,5S)-2-ethylpiperidine-3,4,5-triol
• CAS: 1000855-29-7
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: KNOLQTVRSJRSAM-XZBKPIIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  双丙酮-L-山梨糖 在 吡啶 、 氯化亚砜 、 sodium azide 、 草酰氯 、 palladium 10% on activated carbon 、 20 % Pd(OH)2/C 、 水 、 氢气 、 sodium hexamethyldisilazane 、 溶剂黄146 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~110.0 ℃ 、101.33 kPa 条件下， 反应 56.67h， 生成 (2R,3R,4R,5S)-2-ethylpiperidine-3,4,5-triol
  参考文献：
  名称：

  通过维蒂希反应从L-山梨糖合成1-脱氧野oji霉素衍生物

  摘要：

  描述了从L-山梨糖合成1-脱氧野n霉素（DNJ）衍生物的策略。该序列涉及八个步骤，并以13％至44％的总产率提供了DNJ衍生物。

  DOI：

  10.1080/07328303.2011.619287

文献信息

• <scp>d</scp>-Fructose-6-Phosphate Aldolase-Catalyzed One-Pot Synthesis of Iminocyclitols
  作者：Masakazu Sugiyama、Zhangyong Hong、Pi-Hui Liang、Stephen M. Dean、Lisa J. Whalen、William A. Greenberg、Chi-Huey Wong

  DOI：10.1021/ja073911i

  日期：2007.11.28

  A one-pot chemoenzymatic method for the synthesis of a variety of new iminocyclitols from readily available, non-phosphorylated donor substrates has been developed. The method utilizes the recently discovered fructose-6-phosphate aldolase (FSA), which is functionally distinct from known aldolases in its tolerance of different donor substrates as well as acceptor substrates. Kinetic studies were performed with dihydroxyacetone (DHA), the presumed endogenous substrate for FSA, as well as hydroxy acetone (HA) and 1-hydroxy-2-butanone (HB) as donor substrates, in each case using glyceraidehyde-3-phosphate as acceptor substrate. Remarkably, FSA used the three donor substrates with equal efficiency, with k(cat)/K-M-values of 33, 75, and 20 M-1 s(-1), respectively. This level of donor substrate tolerance is unprecedented for an aldolase. Furthermore, DHA, HA, and HB were accepted as donors in FSA-catalyzed aldol reactions with a variety of azido- and Cbz-amino aldehyde acceptors. The broad substrate tolerance of FSA and the ability to circumvent the need for phosphorylated substrates allowed for one-pot synthesis of a number of known and novel iminocyclitols in good yields, and in a very concise fashion. New iminocyclitols were assayed as inhibitors against a panel of glycosidases. Compounds 15 and 16 were specific alpha-mannosidase inhibitors, and 24 and 26 were potent and selective inhibitors of beta-N-acetylglucosaminidases in the submicromolar range. Facile access to these compounds makes them attractive core structures for further inhibitor optimization.