(3S)-5-[1-tert-butyl-1,1-diphenylsilyl]oxy-1-penten-3-ol | 91376-46-4

• 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: (3S)-5-[1-tert-butyl-1,1-diphenylsilyl]oxy-1-penten-3-ol
• 英文别名: (3S)-5-{[(tert-butyl)(diphenyl)silyl]oxy}pent-1-en-3-ol；(3S)-5-[tert-butyl(diphenyl)silyl]oxypent-1-en-3-ol
• CAS: 91376-46-4
• 化学式: C₂₁H₂₈O₂Si
• 分子量: 340.538
• InChiKey: TWSUVXIYQIOYPJ-GOSISDBHSA-N

物化性质

• 沸点：
  416.3±45.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (3S)-5-[1-tert-butyl-1,1-diphenylsilyl]oxy-1-penten-3-ol 在 咪唑 、 氟化铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.17h， 生成 (S)-3-((tert-butyldimethylsilyl)oxy)pent-4-en-1-ol
  参考文献：
  名称：

  磷酸线虫素关键骨架的合成

  摘要：

  首次采用收敛方法实现了磷酸线虫关键骨架的不对称合成。该合成的显着特征包括酰胺化以在 C-1 位置安装甘氨酸酰胺，Wittig 烯化以形成 C5-C6 键，Julia-Kocienski 烯化以制备 C9-C10 和 C13-C14 键，以及 Takai 烯化和 Sonogashira 耦合分别构建 C17-C18 和 C18-C19 键。所公开的路线是高度模块化的，这将允许合成各种类似物，可用于磷酸线虫的结构-活性关系研究。

  DOI：

  10.1055/a-1881-0529
• 作为产物：
  描述：

  ((2S,3S)-3-(2-(tert-butyldiphenylsilyloxy)ethyl)oxiran-2-yl)methanol 在 咪唑 、 碘 、 锌 作用下， 以 乙醚 、 乙腈 、 乙醇 为溶剂， 反应 2.5h， 生成 (3S)-5-[1-tert-butyl-1,1-diphenylsilyl]oxy-1-penten-3-ol
  参考文献：
  名称：

  First total synthesis of achaetolide

  摘要：

  The first total synthesis of achaetolide, a 10-membered macrolactone was achieved using Mitsunobu reaction and Grubbs ring-closing metathesis reaction as the key steps for ring construction. The desired stereo centres were generated by Jacobsen hydrolytic kinetic resolution, dihydroxylation and Sharpless asymmetric epoxidation reactions. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.127

文献信息

• Total Synthesis of Nonenolide
  作者：Harshadas Mitaram Meshram、Dachepally Aravind Kumar、Palakuri Ramesh

  DOI：10.1002/hlca.200900410

  日期：——

  A novel synthetic route has been reported for the synthesis of nonenolide. The syntheses of fragments were initiated from commercially available and inexpensive starting materials. The synthesis involves key steps like Sharpless epoxidation, Jacobsen's resolution, lactonization, and cross‐metathesis.

  已经报道了用于合成壬烯内酯的新的合成途径。片段的合成从可商购且廉价的起始原料开始。合成涉及关键步骤，如Sharpless环氧化，Jacobsen的拆分，内酯化和交叉复分解。
• Total synthesis of decarestrictine I and botryolide B via RCM protocol
  作者：Palakodety Radha Krishna、T. Jagannadha Rao

  DOI：10.1039/c004556j

  日期：——

  A convergent stereoselective total synthesis of decarestrictine I (1) and botryolide B (1a) invoking a common synthetic strategy is reported. The key steps are: ring-closing metathesis of epoxy dienoic esters obtained through the Yamaguchi esterification of their respective intermediates to furnish the respective Z-macrocycles (2 and 2a) which were further extrapolated to their respective targets.

  会聚立体选择性全合成十碳精胺I（1）和葡萄内酯。乙（1a）报道了一种通用的合成策略。关键步骤是：通过其各自中间体的Yamaguchi酯化反应制得的环氧二烯酸酯的闭环易位，以提供各自的Z-大环（2和2a），并进一步外推至其各自的靶标。
• First stereoselective total synthesis of decarestrictine O via RCM protocol
  作者：Palakodety Radha Krishna、T. Jagannadha Rao

  DOI：10.1016/j.tetlet.2010.05.064

  日期：2010.8

  A convergent first stereoselective total synthesis of decarestrictine O via RCM protocol starting from 1,3-propanediol and propylene oxide is reported.

  据报道，从1，3-丙二醇和环氧丙烷开始，通过RCM协议，对脱卡因汀O进行了聚合的第一立体选择性全合成。
• Total synthesis of Z-isomer of phomolide B
  作者：Debendra K. Mohapatra、D. Prabhakar Reddy、Uttam Dash、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.11.003

  日期：2011.1

  We have achieved the synthesis of Z-isomer of phomolide B during our investigation toward the effect of protecting group on the outcome of ring-closing metathesis reaction. The other key reactions involved are cis-selective partial hydrogenation. Sharpless asymmetric epoxidation, Yamaguchi esteritication, and following 12 longest linear sequence with 18.5% overall yield starting from a known intermediate 20. (C) 2010 Elsevier Ltd. All rights reserved.
• First total synthesis of achaetolide
  作者：S. Chandrasekhar、S.V. Balaji、G. Rajesh

  DOI：10.1016/j.tetlet.2010.07.127

  日期：2010.9

  The first total synthesis of achaetolide, a 10-membered macrolactone was achieved using Mitsunobu reaction and Grubbs ring-closing metathesis reaction as the key steps for ring construction. The desired stereo centres were generated by Jacobsen hydrolytic kinetic resolution, dihydroxylation and Sharpless asymmetric epoxidation reactions. (c) 2010 Elsevier Ltd. All rights reserved.