2,5-Di-O-mesyl-1,3:4,6-di-O-benzylidene-D-mannitol | 151061-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2,5-Di-O-mesyl-1,3:4,6-di-O-benzylidene-D-mannitol
• 英文别名: [(2R,4S,5R)-4-[(2R,4S,5R)-5-methylsulfonyloxy-2-phenyl-1,3-dioxan-4-yl]-2-phenyl-1,3-dioxan-5-yl] methanesulfonate
• CAS: 151061-71-1
• 化学式: C₂₂H₂₆O₁₀S₂
• 分子量: 514.574
• InChiKey: YGOPSNHHGKAASZ-CGXUPHRESA-N

物化性质

• 沸点：
  731.5±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,5-Di-O-mesyl-1,3:4,6-di-O-benzylidene-D-mannitol 在 Lindlar's catalyst 吡啶 、 三乙基硅烷 、 sodium azide 、 三氟化硼乙醚 、 氢气 、 三氯化铁 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 46.5h， 生成 (2R,3S,4S,5R)-1,6-bis(benzyloxy)-3,4-bis((methylsulfonyl)oxy)-N2,N5-ditosylhexane-2,5-diamine
  参考文献：
  名称：

  Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from d-mannitol

  摘要：

  A practical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive D-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzylidene acetal 3 to form dimesylate 4, which was further converted to monoazides and diazides followed by reduction, mesylation, and cyclization to furnish the required compounds in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.035
• 作为产物：
  描述：

  甘露醇 在 硫酸 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 122.0h， 生成 2,5-Di-O-mesyl-1,3:4,6-di-O-benzylidene-D-mannitol
  参考文献：
  名称：

  Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from d-mannitol

  摘要：

  A practical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive D-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzylidene acetal 3 to form dimesylate 4, which was further converted to monoazides and diazides followed by reduction, mesylation, and cyclization to furnish the required compounds in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.035

文献信息

• Studies on the formation of a tricyclic C2-symmetric sulfide
  作者：Caroline L Winn、Jonathan M Goodman

  DOI：10.1016/s0040-4039(01)01455-1

  日期：2001.10

  Attempts to synthesise chiral sulfide 1 from the dimesylate precursor 5, via a cyclisation reaction using sodium sulfide in dimethyl sulfoxide, led to the unexpected formation of an unsymmetrical furan derivative 8. Studies were made into the effect of changing the leaving group, and changing the solvent of reaction. The desired compound could be synthesised in good yields from the xanthate 9 using

  尝试通过使用二甲基亚砜中的硫化钠的环化反应从二甲基磺酸酯前体5合成手性硫化物1，导致意外地形成了不对称的呋喃衍生物8。研究了改变离去基团和改变反应溶剂的作用。可以使用自由基介导的方法从黄原酸酯9以高收率合成期望的化合物。
• Rao, A. V. Rama; Reddy, K. Ashok; Srinivas, N. R., Journal of the Chemical Society. Perkin transactions I, 1993, # 11, p. 1255 - 1260
  作者：Rao, A. V. Rama、Reddy, K. Ashok、Srinivas, N. R.、Gurjar, M. K.、Padmaja, N.、et al.

  DOI：——

  日期：——
• Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from d-mannitol
  作者：Devarajulu Sureshkumar、Susama Maity、Srinivasan Chandrasekaran

  DOI：10.1016/j.tet.2006.08.035

  日期：2006.10

  A practical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive D-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzylidene acetal 3 to form dimesylate 4, which was further converted to monoazides and diazides followed by reduction, mesylation, and cyclization to furnish the required compounds in good yields. (c) 2006 Elsevier Ltd. All rights reserved.