methyl (4S,5R)-(E)-5-tert-butyldimethylsilyloxy-4-methyl-2-heptenoate | 141858-88-0

• 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: methyl (4S,5R)-(E)-5-tert-butyldimethylsilyloxy-4-methyl-2-heptenoate
• CAS: 141858-88-0
• 化学式: C₁₅H₃₀O₃Si
• 分子量: 286.487
• InChiKey: GLRJFABZUJVVSY-LZBRBDLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (4S,5R)-(E)-5-tert-butyldimethylsilyloxy-4-methyl-2-heptenoate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到methyl 5-hydroxy-4-methylhept-2-enoate
  参考文献：
  名称：

  An Enantiocontrolled Route to Protomycinolide IV and Its Presumed Biogenetic Precursors Using (S)-O-Benzylglycidol

  摘要：

  Starting with (S)-O-benzylglycidol (9) as only chiral building block, a formal synthesis of protomycinolide IV (1) and the first syntheses of its presumed biogenetic precursors methyl epimycinonate I (2), methyl mycinonate I (3), methyl mycinonate II (4), and decarboxymycinonic acid III (5), have been achieved via the eight-carbon unit (8) as a common intermediate.

  DOI：

  10.3987/com-91-s80
• 作为产物：
  描述：

  (4S,5R)-(E)-1-benzyloxy-5-tert-butyldimethylsilyloxy-4-methyl-2-heptene 在 manganese(IV) oxide 、 氰化钠 、 氨 、 lithium 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 methyl (4S,5R)-(E)-5-tert-butyldimethylsilyloxy-4-methyl-2-heptenoate
  参考文献：
  名称：

  An Enantiocontrolled Route to Protomycinolide IV and Its Presumed Biogenetic Precursors Using (S)-O-Benzylglycidol

  摘要：

  Starting with (S)-O-benzylglycidol (9) as only chiral building block, a formal synthesis of protomycinolide IV (1) and the first syntheses of its presumed biogenetic precursors methyl epimycinonate I (2), methyl mycinonate I (3), methyl mycinonate II (4), and decarboxymycinonic acid III (5), have been achieved via the eight-carbon unit (8) as a common intermediate.

  DOI：

  10.3987/com-91-s80

文献信息

• One-pot sequential cross-metathesis/hydride reduction: highly stereoselective synthesis of primary (E)-allylic alcohols from terminal olefins
  作者：Tapas Paul、Gopal Sirasani、Rodrigo B. Andrade

  DOI：10.1016/j.tetlet.2008.03.132

  日期：2008.5

  Several di- and trisubstituted primary (E)-allylic alcohols have been prepared from the corresponding terminal olefins in a highly stereoselective manner (>20:1 E/Z) by sequencing olefin cross-metathesis (CM) with hydride reduction (DIBAL-H) in good yields utilizing only commercially available reagents in a one-pot fashion. The method is a reliable alternative to the direct CM of terminal olefins with

  通过以氢化物还原法对烯烃交叉复分解（CM）进行测序（DIBAL-H），从相应的末端烯烃以高度立体选择性的方式（> 20：1 E / Z）制备了几种二和三取代的伯（E）烯丙基醇。）仅使用一锅法仅使用市售试剂即可获得高收率）。该方法是端烯与烯丙醇直接CM的可靠替代方法，后者并不总是立体选择性的，而是高度依赖底物的。
• Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1016/j.tet.2011.01.080

  日期：2011.3

  The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g.. Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology. (C) 2011 Elsevier Ltd. All rights reserved.