[(2R)-2-[(4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(4-methylphenyl)sulfonylamino]ethyl] acetate | 275812-99-2

• 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: [(2R)-2-[(4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(4-methylphenyl)sulfonylamino]ethyl] acetate
• CAS: 275812-99-2
• 化学式: C₁₈H₂₇NO₈S
• 分子量: 417.48
• InChiKey: NBIGSGAMECKFFD-QBPKDAKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R)-2-[(4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(4-methylphenyl)sulfonylamino]ethyl] acetate 在 吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [(3aR,4R,7R,7aR)-7-acetyloxy-2,2-dimethyl-5-(4-methylphenyl)sulfonyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridin-4-yl]methyl acetate
  参考文献：
  名称：

  Use of the N-tosyl-activated aziridine 1,2-dideoxy-1,2-iminomannitol as a synthon for 1-deoxymannojirimycin analogues

  摘要：

  1-Amino-1-deoxy-D-glucitol was converted into the selectively protected title compound 4, an N-tosyl-activated aziridine that readily underwent ring opening with various nucleophiles. Further deprotection of the 5,6-diol moiety followed by ring closure under Mitsunobu conditions afforded the corresponding 6-substituted analogues of 1-deoxymannojirimycin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00130-1
• 作为产物：
  描述：

  1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1,2-(N-p-toluenesulfonyl)imino-D-mannitol 在 Dowex 50X₈-200 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 [(2R)-2-[(4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(4-methylphenyl)sulfonylamino]ethyl] acetate
  参考文献：
  名称：

  Use of the N-tosyl-activated aziridine 1,2-dideoxy-1,2-iminomannitol as a synthon for 1-deoxymannojirimycin analogues

  摘要：

  1-Amino-1-deoxy-D-glucitol was converted into the selectively protected title compound 4, an N-tosyl-activated aziridine that readily underwent ring opening with various nucleophiles. Further deprotection of the 5,6-diol moiety followed by ring closure under Mitsunobu conditions afforded the corresponding 6-substituted analogues of 1-deoxymannojirimycin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00130-1