(2R,6R,3E)-1,7-dibenzyloxyhept-3-ene-2,6-diol | 145306-82-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,6R,3E)-1,7-dibenzyloxyhept-3-ene-2,6-diol
• CAS: 145306-82-7
• 化学式: C₂₁H₂₆O₄
• 分子量: 342.435
• InChiKey: OXYLSMWKIQXBIW-WYIOMSSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  25.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,6R,3E)-1,7-dibenzyloxyhept-3-ene-2,6-diol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 4 A molecular sieve 、 sodium dihydro-bis-(2-methoxyethoxy)aluminate 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Katsuki-Sharpless asymmetric epoxidation of allylic-homoallylic alcohols sharing the central olefinic bond

  摘要：

  Katsuki-Sharpless asymmetric epoxidation of four isomeric chiral allylic-homoallylic diols sharing the central olefinic bond has been examined. Among these, three heptenediols having (3E,2R,6R), (3E,2R,6S), and (3Z,2R,6R) configurations underwent diastereospecific epoxidation to give the corresponding epoxides each as a single epimer in the presence of L-DIPT, but the diol having (3Z,2R,6S) configuration did not show high diastereoselection in the presence of either L- or D-DIPT. Interestingly, (3Z,2R,6R)-diol afforded the same epoxide irrespective of the chirality of DIPT used.

  DOI：

  10.1016/s0040-4039(00)79094-0
• 作为产物：
  描述：

  (R)-4-benzyloxy-3-hydroxy-1-butyne 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,6R,3E)-1,7-dibenzyloxyhept-3-ene-2,6-diol
  参考文献：
  名称：

  Katsuki-Sharpless asymmetric epoxidation of allylic-homoallylic alcohols sharing the central olefinic bond

  摘要：

  Katsuki-Sharpless asymmetric epoxidation of four isomeric chiral allylic-homoallylic diols sharing the central olefinic bond has been examined. Among these, three heptenediols having (3E,2R,6R), (3E,2R,6S), and (3Z,2R,6R) configurations underwent diastereospecific epoxidation to give the corresponding epoxides each as a single epimer in the presence of L-DIPT, but the diol having (3Z,2R,6S) configuration did not show high diastereoselection in the presence of either L- or D-DIPT. Interestingly, (3Z,2R,6R)-diol afforded the same epoxide irrespective of the chirality of DIPT used.

  DOI：

  10.1016/s0040-4039(00)79094-0

文献信息

• Enantioselective Synthesis of 1,5-<i>anti</i>- and 1,5-<i>syn</i>-Diols Using a Highly Diastereoselective One-Pot Double Allylboration Reaction Sequence
  作者：Eric M. Flamme、William R. Roush

  DOI：10.1021/ja028055j

  日期：2002.11.1

  gamma-boryl-substituted allylborane reagents 4 and 11 were generated in situ by the hydroboration of allenes 3 and 10 with diisopinocampheylborane. The keys to the success of this method are the excellent stereocontrol in the allylboration step leading to 5 and the corresponding substituted methallylboronate derived from 11, the stereospecificity of the subsequent allylboration reaction of the substituted

  1,5-二取代 (E)-1,5-anti-pent-2-endiols 1 和 (Z)-1,5-syn-pent-2-endiols 2 的高度非对映选择性和对映选择性合成已通过两种不同的醛与 (E)-γ-(1,3,2-二氧杂硼烷基)-烯丙基]二异松蒎基硼烷 (4) 或 (E)-γ-(4,4,5,5-四苯基-分别为 1,3,2-二氧杂硼烷基)烯丙基]二异松蒎基硼烷 (11)。在所有情况下，以 63-95% 的产率获得指定的二醇 1 和 2，具有 89-96% ee 和 >/=20:1 的非对映选择性。双功能 γ-硼基取代的烯丙基硼烷试剂 4 和 11 是通过丙二烯 3 和 10 与二异松蒎基硼烷的硼氢化反应原位生成的。该方法成功的关键是烯丙基硼化步骤中出色的立体控制导致 5 和相应的取代的甲基烯丙基硼酸酯衍生自 11，