N-[(1R)-1-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(2-methylpropan-2-yl)oxy]ethyl]-4-methylbenzenesulfonamide | 275812-82-3

• 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: N-[(1R)-1-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(2-methylpropan-2-yl)oxy]ethyl]-4-methylbenzenesulfonamide
• CAS: 275812-82-3
• 化学式: C₂₃H₃₇NO₇S
• 分子量: 471.615
• InChiKey: CWUOBDUBWQIQFL-UAFMIMERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[(1R)-1-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(2-methylpropan-2-yl)oxy]ethyl]-4-methylbenzenesulfonamide 在 Dowex 50X₈-200 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (3aR,4R,7R,7aR)-2,2-dimethyl-5-(4-methylphenyl)sulfonyl-4-[(2-methylpropan-2-yl)oxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridin-7-ol
  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-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-toluenesulfonyl)amino-D-glucitol 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 N-[(1R)-1-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(2-methylpropan-2-yl)oxy]ethyl]-4-methylbenzenesulfonamide
  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

文献信息

• Use of the N-tosyl-activated aziridine 1,2-dideoxy-1,2-iminomannitol as a synthon for 1-deoxymannojirimycin analogues
  作者：Gert J Joly、Koen Peeters、Hua Mao、Thierry Brossette、Georges J Hoornaert、Frans Compernolle

  DOI：10.1016/s0040-4039(00)00130-1

  日期：2000.3

  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.