[(2R,3S,4S,5R)-3,4-dihydroxy-5-methylsulfonyloxy-1,6-bis(phenylmethoxy)hexan-2-yl] methanesulfonate | 257881-05-3

• 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: [(2R,3S,4S,5R)-3,4-dihydroxy-5-methylsulfonyloxy-1,6-bis(phenylmethoxy)hexan-2-yl] methanesulfonate
• CAS: 257881-05-3
• 化学式: C₂₂H₃₀O₁₀S₂
• 分子量: 518.606
• InChiKey: XNOSYQRCGWGAEA-GXRSIYKFSA-N

物化性质

• 沸点：
  755.7±60.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R)-3,4-dihydroxy-5-methylsulfonyloxy-1,6-bis(phenylmethoxy)hexan-2-yl] methanesulfonate 在 Lindlar's catalyst 吡啶 、 sodium azide 、 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 45.5h， 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 三乙基硅烷 、 硫酸 、 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 123.0h， 生成 [(2R,3S,4S,5R)-3,4-dihydroxy-5-methylsulfonyloxy-1,6-bis(phenylmethoxy)hexan-2-yl] methanesulfonate
  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

• 1,3:4,6-Di-O-benzylidene-d-mannitol as a source for novel chiral intermediates through regioselective reductive cleavage
  作者：Appu Aravind、Sundarababu Baskaran

  DOI：10.1016/j.tetlet.2004.12.036

  日期：2005.1

  Synthetically useful chiral intermediates have been synthesized starting from 1,3:4.6-di-O-benzylidene-D-mannitol by yields. regioselective reductive cleavage using (BF3Et2O)-Et-. and Et3SiH in high (C) 2004 Elsevier Ltd. All rights reserved.
• 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.