1,2:4,5-di-O-isopropylidene-(+)-epi-quercitol | 229612-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:4,5-di-O-isopropylidene-(+)-epi-quercitol
• CAS: 229612-87-7
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: GZAUSEVVFGFLES-SVSWQMSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,2:4,5-di-O-isopropylidene-(+)-epi-quercitol 在 platinum(IV) oxide 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  从（+）-表-和（-）-维生素-槲皮醇方便地合成3-和6-脱氧-D-肌醇磷酸酯类似物。

  摘要：

  从通过肌醇生物转化而容易产生的（+）-表-和（-）-维-槲皮醇开始，一些生物学上有趣的磷酸盐和多磷酸盐类似物，包括3的Ins（1,4,5）P（3）衍生物-脱氧-和6-脱氧-D-肌醇可以容易地以常规方式制备。此外，3-脱氧Ins（1,4,5）P（3）在C-2处的化学修饰提供了2-电子异构体，2-脱氧和2-脱氧-2-氟形式。测定了获得的八种多磷酸盐类似物对PDH-Pase和PDH-K以及G6Pase的生物学活性，但没有一个被证明是阳性的。

  DOI：

  10.1016/j.bmcl.2006.06.096
• 作为产物：
  描述：

  2-甲氧基丙烯 、 (1R,2S,4S,5S)-cyclohexane-1,2,3,4,5-pentol 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以30.4%的产率得到1,2:3,4-di-O-isopropylidene-(+)-epi-quercitol
  参考文献：
  名称：

  SYNTHESIS OF 1- AND 3-C-(AMINOMETHYL)-1,2,3,4,5-CYCLOHEXANEPENTOLS FROM (+)-epi-QUERCITOL1

  摘要：

  Oxidation of three di-O-isopropylidene derivatives 2a-4a, newly derived from (+)-epi-quercitol (1), with acetic anhydride in DMSO gave the corresponding ketones 5-7, which underwent aldol-type condensation with nitromethane under basic conditions to give selectively the protected derivatives 8a-10a of C-nitromethyl-1,2,3,4,5-cyclohexanepentols, respectively. On treatment with diazomethane in DMSO, the ketones 6 and 7 gave single spiro epoxides 11 and 12, the structures of which were confirmed by converting them into new C-(azidomethyl)cyclohexanepentols 16 and 17. The nitro compounds were hydrogenated in the presence of Raney nickel to give the amines isolated as the N-acetyl derivatives. Deprotection gave three new 1- and 3-C-aminomethyldeoxyinositols 15c-17c. The aminocyclitols obtained and their N-acetyl derivatives were assayed for inhibitory activity against examples of glycosidases.

  DOI：

  10.1081/car-100108284

文献信息

• Synthesis and evaluation of glucocerebrosidase inhibitory activity of anhydro deoxyinositols from (+)-epi-and(−)-vibo-quercitols
  作者：Seiichiro Ogawa、Satoko Uetsuki、Yoji Tezuka、Takayuki Morikawa、Atsushi Takahashi、Kiyoshi Sato

  DOI：10.1016/s0960-894x(99)00223-1

  日期：1999.6

  Twelve 1,2- and 2,3-anhydro-1,2,3,4,5-cyclohexanepentols were synthesized from (+)-epi- and (-)-vibo-quercitols, readily available by bioconversion of myo-inositol, and assayed for inhibitory activity against glucocerebrosidase (mouse liver). Among them 1L-1,2-anhydro-1,2,4/3,5-cyclohexanepentol, the 3-deoxy derivative of the irreversible inhibitor conduritol B epoxide (CBE), has been demonstrated to be a highly potent and specific inhibitor, almost comparable to the parent compound. (C) 1999 Elsevier Science Ltd. All rights reserved.