methyl (3R,5R)-6-(benzyloxy)-3-methyl-5-(tetrahydro-2H-pyran-2-yloxy)hexanoate | 1608093-64-6

• 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: methyl (3R,5R)-6-(benzyloxy)-3-methyl-5-(tetrahydro-2H-pyran-2-yloxy)hexanoate
• 英文别名: Methyl (3r,5r)-6-benzyloxy-3-methyl-5-(tetra-hydro-2h-pyran-2-yloxy)hexanoate；methyl (3R,5R)-3-methyl-5-(oxan-2-yloxy)-6-phenylmethoxyhexanoate
• CAS: 1608093-64-6
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: ZNSXNLJMWAEJSO-PGBVBIMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3R,5R)-6-(benzyloxy)-3-methyl-5-(tetrahydro-2H-pyran-2-yloxy)hexanoate 在 chromium(VI) oxide 、 titanium(IV) isopropylate 、 sodium acetate trihydrate 、 甲基磺酰氯 、 三乙胺 、 环己基溴化镁 作用下， 以 四氢呋喃 、 氯仿 、 水 、 丙酮 为溶剂， 反应 20.08h， 生成 (2R,4R,10S)-1-benzyloxy-4-methyl-2,10-bis(tetrahydro-2H-pyran-2-yloxy)undecan-6-one
  参考文献：
  名称：

  New asymmetric synthesis of a pheromone component of the shield bug Cantao Parentum

  摘要：

  A novel procedure has been developed for the synthesis of (2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro[5.5]undecane, a pheromone component of the shield bug Cantao Parentum, through intermediate cyclopropanol derivatives in the key stages of carbon chain construction and introduction of functional groups.

  DOI：

  10.1134/s1070428014030178
• 作为产物：
  描述：

  (4R,6R)-6-(benzyloxymethyl)-4-methyltetrahydro-2H-pyran-2-one 在 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 52.0h， 生成 methyl (3R,5R)-6-(benzyloxy)-3-methyl-5-(tetrahydro-2H-pyran-2-yloxy)hexanoate
  参考文献：
  名称：

  New asymmetric synthesis of a pheromone component of the shield bug Cantao Parentum

  摘要：

  A novel procedure has been developed for the synthesis of (2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro[5.5]undecane, a pheromone component of the shield bug Cantao Parentum, through intermediate cyclopropanol derivatives in the key stages of carbon chain construction and introduction of functional groups.

  DOI：

  10.1134/s1070428014030178

文献信息

• Functionalized 2-Substituted Allyl Bromides in the Barbier Allylation of (R)-2,3-O-Isopropylideneglyceraldehyde. Synthesis of the C8–C17, C8–C18, and C5–C17 Building Blocks of Laulimalides and Their Synthetic Analogs
  作者：I. V. Mineyeva

  DOI：10.1134/s1070428019040195

  日期：2019.4

  Several new 2-substituted allyl bromides were synthesized through cyclopropanol intermediates and were then involved in the Barbier allylation of (R)-2,3-O-isopropylideneglyceraldehyde in the presence of zinc in a mixture of tetrahydrofuran and saturated aqueous ammonium chloride to obtain the corresponding homoallylic alcohols with high diastereoselectivity. The possibility of using the latter as

  通过环丙醇中间体合成了几种新的2-取代的烯丙基溴，然后在四氢呋喃和饱和氯化铵水溶液的混合物中，在锌的存在下，参与（R）-2,3- O-异亚丙基甘油醛的Barbier烯丙基化反应。具有高非对映选择性的相应的均烯丙基醇。证明了将后者用作大环抗肿瘤剂（月桂酰亚胺）及其合成类似物的基础。