(4S,5R)-(E)-5-tert-butyldimethylsilyloxy-4-methyl-2-hepten-1-ol | 141858-87-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4S,5R)-(E)-5-tert-butyldimethylsilyloxy-4-methyl-2-hepten-1-ol
• 英文别名: (4S,5R,E)-5-[(tert-butyldimethylsilyl)oxy]-4-methylhept-2-en-1-ol；(E,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-4-methylhept-2-en-1-ol
• CAS: 141858-87-9
• 化学式: C₁₄H₃₀O₂Si
• 分子量: 258.476
• InChiKey: SSQPRYJQIDGLOV-CCJARXIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R)-(E)-5-tert-butyldimethylsilyloxy-4-methyl-2-hepten-1-ol 在 盐酸 manganese(IV) oxide 、 氰化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 5-hydroxy-4-methylhept-2-enoate
  参考文献：
  名称：

  拟霉素的生物合成中拟议中间体的立体化学

  摘要：

  从灰单孢菌（Micromonospora griserubida sp。）的培养滤液中分离出的霉素霉素的生​​物合成中拟议中间体的立体化学。已经建立。

  DOI：

  10.1016/s0040-4039(00)99306-7
• 作为产物：
  描述：

  methyl (4S,5R)-(E)-5-tert-butyldimethylsilyloxy-4-methyl-2-heptenoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4S,5R)-(E)-5-tert-butyldimethylsilyloxy-4-methyl-2-hepten-1-ol
  参考文献：
  名称：

  一锅顺序交叉复分解/氢化物还原：由末端烯烃高度立体选择性地合成伯（E）-烯丙基醇

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2008.03.132

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。
• Stereochemistry of the proposed intermediates in the biosynthesis of mycinamicins
  作者：Seiichi Takano、Yoshinori Sekiguchi、Youichi Shimazaki、Kunio Ogasawara

  DOI：10.1016/s0040-4039(00)99306-7

  日期：1989.1

  Stereochemistry of the proposed intermediates in the biosynthesis of mycinamicins isolated from the culture filtrate of Micromonospora griserubida sp. has been established.

  从灰单孢菌（Micromonospora griserubida sp。）的培养滤液中分离出的霉素霉素的生​​物合成中拟议中间体的立体化学。已经建立。
• Stereoselective Total Synthesis of the Non-Contiguous Polyketide Natural Product (-)-Dolabriferol
  作者：Naresh Gantasala、Suresh Borra、Srihari Pabbaraja

  DOI：10.1002/ejoc.201701748

  日期：2018.3.14

  The stereoselective total synthesis of dolabriferol has been accomplished in 17 steps, by an approach that is both divergent and convergent. The effect of protecting groups on the alcohol substrate played a pivotal role for Yamaguchi esterification.

  多拉布雷佛罗的立体选择性全合成已通过发散和收敛的方法在17个步骤中完成。保护基在醇底物上的作用在山口酯化中起关键作用。
• 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.
• An Enantiocontrolled Route to Protomycinolide IV and Its Presumed Biogenetic Precursors Using (S)-O-Benzylglycidol
  作者：Seiichi Takano、Yoshinori Sekiguchi、Youicho Shimazaki、Kunio Ogasawara

  DOI：10.3987/com-91-s80

  日期：——

  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.