1-(acetamidomethyl)-2-deoxy-D-chiro-inositol | 415726-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(acetamidomethyl)-2-deoxy-D-chiro-inositol
• 英文别名: N-[[(1S,2R,3R,4S,5R)-1,2,3,4,5-pentahydroxycyclohexyl]methyl]acetamide
• CAS: 415726-97-5
• 化学式: C₉H₁₇NO₆
• 分子量: 235.237
• InChiKey: NTUYDYIPZNMMBC-WUNNTHRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  130
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-(acetamidomethyl)-2-deoxy-D-chiro-inositol 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 72.0h， 以36 mg的产率得到hexa-[cf'1]N,O-acetyl-1-(aminomethyl)-2-deoxy-D-chiro-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：

  2,3:4,5-di-O-isopropylidene-(+)-epi-quercitol 在 Raney nickel T-4 氢气 、 sodium methylate 、 乙酸酐 、 溶剂黄146 、 二甲基亚砜 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 131.5h， 生成 1-(acetamidomethyl)-2-deoxy-D-chiro-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