N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride | 1425499-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride
• 英文别名: (1S,2S,3S,6R)-4-methyl-6-(octylamino)cyclohex-4-ene-1,2,3-triol;hydrochloride
• CAS: 1425499-48-4
• 化学式: C₁₅H₂₉NO₃*ClH
• 分子量: 307.861
• InChiKey: QKULAKIXDABUBD-SJFOYXCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  72.7
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  原栎醇 在 吡啶 、 正丁基锂 、 sodium borohydrid 、 camphor-10-sulfonic acid 、 溴 、 sodium methylate 、 三氧化硫吡啶 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 六甲基磷酰三胺 、 正己烷 、 水 、 二甲基亚砜 、 丙酮 、 乙腈 为溶剂， 反应 138.5h， 生成 N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride
  参考文献：
  名称：

  Concise syntheses of potent chaperone drug candidates, N-octyl-4-epi-β-valinenamine (NOEV) and its 6-deoxy derivative, from (+)-proto-quercitol

  摘要：

  Described are the efficient syntheses of beta-galactose-type unsaturated carbasugar amine, N-octyl-4-epi-beta-valienamine (1a, NOEV) and 6-deoxy NOEV (12), starting from (+)-proto-quercitol (2), which is readily provided by the bioconversion of myo-inositol. NOEV is a potent chemical chaperone drug candidate for G(M1)-gangliosidosis. An intermediate alkadiene benzoate was prepared from 2 in five steps, with the key step being a Wittig reaction with an enol ester. The 6-deoxy derivative 12 was conveniently synthesized from the versatile intermediate dibromo compound 6, which was also an intermediate in the synthesis of NOEV. Enzyme inhibition assays demonstrated that 12 possessed stronger inhibitory activity than the parent 1a, suggesting that the C-6 position of the 4-epi-beta-valienamine-type inhibitor could have hydrophobic interactions at the beta-galactosidase active site residues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.12.010

文献信息

• Concise syntheses of potent chaperone drug candidates, N-octyl-4-epi-β-valinenamine (NOEV) and its 6-deoxy derivative, from (+)-proto-quercitol
  作者：Shinichi Kuno、Atsushi Takahashi、Seiichiro Ogawa

  DOI：10.1016/j.carres.2012.12.010

  日期：2013.3

  Described are the efficient syntheses of beta-galactose-type unsaturated carbasugar amine, N-octyl-4-epi-beta-valienamine (1a, NOEV) and 6-deoxy NOEV (12), starting from (+)-proto-quercitol (2), which is readily provided by the bioconversion of myo-inositol. NOEV is a potent chemical chaperone drug candidate for G(M1)-gangliosidosis. An intermediate alkadiene benzoate was prepared from 2 in five steps, with the key step being a Wittig reaction with an enol ester. The 6-deoxy derivative 12 was conveniently synthesized from the versatile intermediate dibromo compound 6, which was also an intermediate in the synthesis of NOEV. Enzyme inhibition assays demonstrated that 12 possessed stronger inhibitory activity than the parent 1a, suggesting that the C-6 position of the 4-epi-beta-valienamine-type inhibitor could have hydrophobic interactions at the beta-galactosidase active site residues. (C) 2012 Elsevier Ltd. All rights reserved.