(3R,4R,5R)-3,4-dihydroxy-5-(2-hydroxyethyl)piperidine | 1338213-03-8

• 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)piperidine
• 英文别名: (3R,4R,5R)-5-(2-hydroxyethyl)piperidine-3,4-diol；5-epi-homoisofagomine
• CAS: 1338213-03-8
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: MMWSFXGSQAOMQI-FSDSQADBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  11
• 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：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-3,4-dihydroxy-5-(2-hydroxyethyl)piperidine 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以81%的产率得到(3R,4R,5R)-3,4-dihydroxy-5-(2-hydroxyethyl)piperidine 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
• 作为产物：
  描述：

  (4S,4'R,5R)-2,2,2',2'-tetramethyl-5-(1-nitropent-4-en-2-yl)-4,4'-bi(1,3-dioxolane) 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 20% palladium hydroxide-activated charcoal 、 potassium tert-butylate 、 水 、 氢气 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 63.5h， 生成 (3R,4R,5R)-3,4-dihydroxy-5-(2-hydroxyethyl)piperidine
  参考文献：
  名称：

  Synthesis of isofagomine and some new azasugars as glycosidase inhibitors from d-mannitol derived nitroolefins

  摘要：

  The synthesis of isofagomine, epi-isofagomine and isofagomine analogues along with some new azasugars from two different vinyl nitro compounds, that were derived from D-mannitol, has been carried out. Two different synthetic strategies were followed for each of the vinyl-nitro precursors. Many of the azasugars synthesized showed inhibition in the micromolar range when tested against various glycosidase enzymes, opening up the possibility of modifying structural features for better and selective inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.021

文献信息

• Novel Compositions for Preventing and/or Treating Lysosomal Storage Disorders
  申请人：Amicus Therapeutical, Inc.

  公开号：US20180334432A1

  公开（公告）日：2018-11-22

  The present invention provides novel compositions as well as methods for preventing and/or treating lysosomal storage disorders. In particular, the present invention provides methods for preventing and/or treating Gaucher's disease.