(S)-1,4-di-O-mesyl-O-(methoxymethyl)-1,2,4-butanetriol | 532983-45-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (S)-1,4-di-O-mesyl-O-(methoxymethyl)-1,2,4-butanetriol
• CAS: 532983-45-2
• 化学式: C₈H₁₈O₈S₂
• 分子量: 306.358
• InChiKey: OZBBAEPOMGXOLF-QMMMGPOBSA-N

物化性质

• 沸点：
  501.5±50.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.68
• 重原子数：
  18.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-1,4-di-O-mesyl-O-(methoxymethyl)-1,2,4-butanetriol 在 双氧水 、 sodium hydride 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (1RS,3S)-3-methoxymethoxy-1-phenylphospholane 1-oxide
  参考文献：
  名称：

  Synthesis of Functionalized Phospholane Oxides and Phosphorinane Oxides from 1,4- and 1,5-Di-O-Mesyloxy Compounds

  摘要：

  Treatment of 1,4-di-0-mesyl-2,3-di-O-methyl-L-threitol (8b) with phenylphosphine in the presence of sodium hydride in DMSO, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane 1-oxide (7), while the same treatment of 1,5-di-O-mesyl-2,3,4-tri-O-methyl-mesoxylitol (11b) provided 2,3,4-trimethoxy-1-phenylphosphorinane 1-oxide (14).

  DOI：

  10.3987/com-06-s(o)28
• 作为产物：
  描述：

  dimethyl 2-O-(methoxymethyl)-L-malate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-1,4-di-O-mesyl-O-(methoxymethyl)-1,2,4-butanetriol
  参考文献：
  名称：

  Synthesis of Functionalized Phospholane Oxides and Phosphorinane Oxides from 1,4- and 1,5-Di-O-Mesyloxy Compounds

  摘要：

  Treatment of 1,4-di-0-mesyl-2,3-di-O-methyl-L-threitol (8b) with phenylphosphine in the presence of sodium hydride in DMSO, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane 1-oxide (7), while the same treatment of 1,5-di-O-mesyl-2,3,4-tri-O-methyl-mesoxylitol (11b) provided 2,3,4-trimethoxy-1-phenylphosphorinane 1-oxide (14).

  DOI：

  10.3987/com-06-s(o)28

文献信息

• A comparative study of the stereoselective addition of trimethylsilyl cyanide and diethylaluminum cyanide to chiral cyclic nitrones
  作者：Pedro Merino、Tomas Tejero、Julia Revuelta、Pilar Romero、Stefano Cicchi、Vanni Mannucci、Alberto Brandi、Andrea Goti

  DOI：10.1016/s0957-4166(02)00832-7

  日期：2003.2

  The mild cyanating agent trimethylsilyl cyanide adds with total stereo selectivity to alpha-alkoxy cyclic nitrones to afford the corresponding trans-hydroxyaminonitriles. The addition of Lewis acids to precomplexing the nitrones does not affect the stereoselectivity of these additions significantly. In all of the cases examined, excellent yields of diastereomerically homogeneous products were obtained. On the other hand, the use of diethylaluminum cyanide as cyanating agent leads to low diastereoselectivities. Both NMR studies and theoretical calculations show that whereas the addition of trimethylsilyl cyanide takes place through a concerted mechanism, in the addition of diethylaluminum cyanide, a complex is formed prior to the intramolecular delivery of the cyanide ion. (C) 2003 Elsevier Science Ltd. All rights reserved.