(2R,3S,4S,5S)-2,3:4,5-bis(isopropylidenedioxy)-1-cyclohexanone | 415726-79-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5S)-2,3:4,5-bis(isopropylidenedioxy)-1-cyclohexanone
• 英文别名: (1S,2S,6R,9S)-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-one
• CAS: 415726-79-3
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: COXSXIHCKVBZHZ-AATLWQCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5S)-2,3:4,5-bis(isopropylidenedioxy)-1-cyclohexanone 在 Raney nickel T-4 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 172.0h， 生成 hexa-N,O-acetyl-1-(aminomethyl)-3-deoxy-L-neo-inositol
  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
• 作为产物：
  描述：

  (1R,2S,4S,5S)-cyclohexane-1,2,3,4,5-pentol 在 乙酸酐 、 对甲苯磺酸 、 二甲基亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (2R,3S,4S,5S)-2,3:4,5-bis(isopropylidenedioxy)-1-cyclohexanone
  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 OF 1- AND 3-C-(AMINOMETHYL)-1,2,3,4,5-CYCLOHEXANEPENTOLS FROM (+)-epi-QUERCITOL1
  作者：Seiichiro Ogawa、Hiroshi Aoyama、Yoji Tezuka

  DOI：10.1081/car-100108284

  日期：——

  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.