(4S,5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane | 170384-62-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (4S,5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane
• 英文别名: [(4S,5S)-5-diethoxyphosphoryl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 170384-62-0
• 化学式: C₁₀H₂₁O₆P
• 分子量: 268.247
• InChiKey: VUEZDPSZVRFVEC-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 在 吡啶 、 4-二甲氨基吡啶 、 三正丁基氢锡 、 sodium iodide 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4S,5S)-4-diethylphosphono-5-methyl-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

  摘要：

  Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD-mix -alpha or -beta reagent was examined to give a series of optically active threo-alpha,beta-dihydroxyphosphonates. Good enantioselectivity (>88% eel was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10341-6
• 作为产物：
  描述：

  亚甲基二磷酸四乙酯 在 ruthenium trichloride 、 potassium osmate(VI) sodium tetrahydroborate 、 sodium periodate 、 AD-mix-α 、 正丁基锂 、 甲基磺酰胺 、 camphor-10-sulfonic acid 作用下， 以 甲醇 、 四氯化碳 、 乙醚 、 正己烷 、 水 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 73.7h， 生成 (4S,5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

  摘要：

  Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD-mix -alpha or -beta reagent was examined to give a series of optically active threo-alpha,beta-dihydroxyphosphonates. Good enantioselectivity (>88% eel was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10341-6

文献信息

• Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of vinylphosphonates. An application to the stereocontrolled synthesis of (4S,5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane
  作者：Tsutomu Yokomatsu、Yoshinori Yoshida、Kenji Suemune、Takehiro Yamagishi、Shiroshi Shibuya

  DOI：10.1016/0957-4166(95)00014-g

  日期：1995.2

  The asymmetric dihydroxylation (AD) reaction of vinylphosphonates with AD-mix-α and -β reagents was successfully applied to the enantioselective synthesis of threo-α, β-dihydroxyphosphonates. β-Aryl substituents on the vinyl phosphonates were found to be good directors for the reaction with respect to the yield and enantioselectivity. The utility of chiral α, β-dihydroxyphosphonate 2c was illustrated

  与AD混合-α和-β试剂vinylphosphonates的不对称二羟基化（AD）反应成功地应用于的对映选择性合成苏- α，β-dihydroxyphosphonates。发现乙烯基膦酸酯上的β-芳基取代基在产率和对映选择性方面是反应的良好指导。通过立体控制合成（4 S，5 S）-4-二乙基膦酰基-2,2-二甲基-5-羟甲基-1,3-二氧戊环6（一种可能有用的ron ），说明了手性α，β-二羟基膦酸酯2c的用途。 α-杂原子取代的膦酸酯的不对称合成。