3,4-O-isopropylidene-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide | 1350889-95-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-O-isopropylidene-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide
• CAS: 1350889-95-0
• 化学式: C₁₀H₁₅BrO₄
• 分子量: 279.131
• InChiKey: YWSGFFUZLQSOMS-XSPKLOCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  辛胺 、 3,4-O-isopropylidene-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide 、 溶剂黄146 在 potassium carbonate 作用下， 以 乙腈 、 水 为溶剂， 反应 26.0h， 以52%的产率得到N-octyl-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine acetic acid
  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
• 作为产物：
  描述：

  原栎醇 在 吡啶 、 正丁基锂 、 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 、 正己烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 114.5h， 生成 3,4-O-isopropylidene-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide
  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

• Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-β-valienamine (NOEV) and N-octyl-β-valienamine (NOV)
  作者：Shinichi Kuno、Atsushi Takahashi、Seiichiro Ogawa

  DOI：10.1016/j.bmcl.2011.09.067

  日期：2011.12

  (+)-proto-Quercitol (1) and (-)-vibo-quercitol (2), both of which could be readily prepared by the bioconversion of myo-inositol, were successfully converted into the corresponding 4-methylenecyclohex-5-ene-1,2,3-triol derivatives. These compounds were demonstrated to be suitable precursors, preserving their configurations, for bioactive carba-aminosugars such as the potent chemical chaperone drug candidates, N-octyl-4-epi-beta-valienamine (NOEV, 3) and N-octyl-beta-valienamine (NOV, 4). (C) 2011 Elsevier Ltd. All rights reserved.

  (+)-原儿茶糖苷醇(1)和(-)-威博儿茶糖苷醇(2)，这两种糖苷均可以通过肌醇的生物转化简便制备，成功转化为了相应的4-甲基环己-5-烯-1,2,3-三醇衍生物。研究证明，这些化合物在保留其构型的情况下，适合作为具有生物活性的氨基糖（如强效化学伴侣药物候选物N-辛基-4-表-β-戊吡胺醇(3)和N-辛基-β-戊吡胺醇(4)）的前体。 (以上译文仅供参考，英文原文版权为2011 Elsevier Ltd.所有，保留所有权利。)