2,6-di-O-benzoyl-3,4-O-isopropylidene-5a-carba-α-L-arabino-hex-5(5a)-enopyranosyl bromide | 1393710-17-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-di-O-benzoyl-3,4-O-isopropylidene-5a-carba-α-L-arabino-hex-5(5a)-enopyranosyl bromide
• CAS: 1393710-17-2
• 化学式: C₂₄H₂₃BrO₆
• 分子量: 487.347
• InChiKey: OLRODFZDFSCFQU-ANULTFPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,6-di-O-benzoyl-3,4-O-isopropylidene-5a-carba-α-L-arabino-hex-5(5a)-enopyranosyl bromide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以44%的产率得到1,2-epoxy-3,4-O-isopropylidene-5a-carba-β-L-arabino-hex-5(5a)-enopyranose
  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：

  sodium benzoate 、 2-O-benzoyl-3,4-O-isopropylidene-6-bromo-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide 、 2-O-benzoyl-3,4-O-isopropylidene-6-bromo-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosyl bromide 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以48%的产率得到2,6-di-O-benzoyl-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