(S)-3-(allyloxy)-2-hydroxypropyl benzoate | 204070-27-9

• 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: (S)-3-(allyloxy)-2-hydroxypropyl benzoate
• 英文别名: (S)-1-benzoyloxy-3-allyloxypropan-2-ol；[(2S)-2-hydroxy-3-prop-2-enoxypropyl] benzoate
• CAS: 204070-27-9
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: LWTFFJGXHDQLFL-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(allyloxy)-2-hydroxypropyl benzoate 在 氢氧化钾 、 4 A molecular sieve 、 silver perchlorate 、 sodium hydride 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 生成 (3R,4S,5R,6R)-2-((R)-1-Allyloxymethyl-2-tetradecyloxy-ethoxy)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran
  参考文献：
  名称：

  A Glucose-Containing Ether Lipid (Glc-PAF) as an Antiproliferative Analogue of the Platelet-Activating Factor

  摘要：

  A new group of active substances, to which 1 belongs, inhibit cell proliferation and initiate programmed cell death (apoptosis) in keratinocytes. The glucosylated phospholipid 1 was synthesized from (S)-isopropylideneglycerol in nine steps with an overall yield of 25 %.

  DOI：

  10.1002/(sici)1521-3773(19980216)37:3<351::aid-anie351>3.0.co;2-p
• 作为产物：
  描述：

  (S)-4-((allyloxy)methyl)-2,2-dimethyl-1,3-dioxolane 在 吡啶 、 4-二甲氨基吡啶 、 水 、 溶剂黄146 作用下， 生成 (S)-3-(allyloxy)-2-hydroxypropyl benzoate
  参考文献：
  名称：

  A Glucose-Containing Ether Lipid (Glc-PAF) as an Antiproliferative Analogue of the Platelet-Activating Factor

  摘要：

  A new group of active substances, to which 1 belongs, inhibit cell proliferation and initiate programmed cell death (apoptosis) in keratinocytes. The glucosylated phospholipid 1 was synthesized from (S)-isopropylideneglycerol in nine steps with an overall yield of 25 %.

  DOI：

  10.1002/(sici)1521-3773(19980216)37:3<351::aid-anie351>3.0.co;2-p

文献信息

• Reagent controlled stereoselective synthesis of teichoic acid α-(1,2)-glucans
  作者：Liming Wang、Francesca Berni、Jacopo Enotarpi、Hermen S. Overkleeft、Gijs van der Marel、Jeroen D. C. Codée

  DOI：10.1039/d0ob00240b

  日期：——

  Additive controlled glycosylation reactions are used for the construction of α-(1,2)-glucosidic linkages, such as those featuring in E. faecalis lipoteichoic acid.

  添加剂控制的糖基化反应用于构建α-(1,2)-葡萄糖苷键，例如在E. faecalis脂肽类脂酸中出现的那些。
• Enzymatic synthesis of both enantiomeric forms of 3-allyloxy-propane-1,2-diol
  作者：Silvana Casati、Enzo Santaniello、Pierangela Ciuffreda

  DOI：10.1016/j.tetasy.2012.03.008

  日期：2012.3

  The stereoselective synthesis of (S)- and (R)-3-allyloxy-propane-1,2-diol has been accomplished in four steps from (RS)-3-allyloxy-propane-1,2-diol. Only one intermediate, namely 1-benzoyloxy-3-allyloxy-2-propanone has been prepared by a chemical reaction, that is, pyridinium chlorochromate oxidation of 1-benzoyloxy-3-allyloxypropan-2-ol. All of the remaining reactions (regioselective acylations, asymmetric bioreduction of prochiral ketones, and enzymatic alcoholysis) have been carried out in the presence of biocatalysts. (C) 2012 Elsevier Ltd. All rights reserved.
• A Glucose-Containing Ether Lipid (Glc-PAF) as an Antiproliferative Analogue of the Platelet-Activating Factor
  作者：Michael Mickeleit、Thomas Wieder、Michael Arnold、Christoph C. Geilen、Johann Mulzer、Werner Reutter

  DOI：10.1002/(sici)1521-3773(19980216)37:3<351::aid-anie351>3.0.co;2-p

  日期：1998.2.16

  A new group of active substances, to which 1 belongs, inhibit cell proliferation and initiate programmed cell death (apoptosis) in keratinocytes. The glucosylated phospholipid 1 was synthesized from (S)-isopropylideneglycerol in nine steps with an overall yield of 25 %.