(S)-1-[1,3]dithian-2-yl-4-(trimethylsilanylmethyl)pent-4-en-2-ol | 617715-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: (S)-1-[1,3]dithian-2-yl-4-(trimethylsilanylmethyl)pent-4-en-2-ol
• 英文别名: (2S)-1-(1,3-dithian-2-yl)-4-(trimethylsilylmethyl)pent-4-en-2-ol
• CAS: 617715-03-4
• 化学式: C₁₃H₂₆OS₂Si
• 分子量: 290.566
• InChiKey: QEJWGJMAKVKRHU-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-[1,3]dithian-2-yl-4-(trimethylsilanylmethyl)pent-4-en-2-ol 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 methyloxirane 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 ((S)-3-Bromomethyl-1-[1,3]dithian-2-ylmethyl-but-3-enyloxy)-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Studies for the enantiocontrolled preparation of substituted tetrahydropyrans: applications for the synthesis of leucascandrolide A macrolactone

  摘要：

  Strategies for the stereocontrolled preparations of 2,6-cis- and 2,6-trans-substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in S-E' reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at -78 degrees C yield nonracemic 1,5-diols for chemoselective internal backside displacements. This concept is developed as a flexible and reliable strategy in studies toward leucascandrolide A macrolactone 2 via the sequential applications of S-E' reactions leading to the C-1-C-9 aldehyde 14, and the bis-tetrahydropyran 59, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.020
• 作为产物：
  描述：

  (2-溴代烯丙基)三甲硅烷 、 (R)-2-((1,3-dithian-2-yl)methyl)oxirane 在 magnesium 、 copper(l) iodide 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以75%的产率得到(S)-1-[1,3]dithian-2-yl-4-(trimethylsilanylmethyl)pent-4-en-2-ol
  参考文献：
  名称：

  Studies for the enantiocontrolled preparation of substituted tetrahydropyrans: applications for the synthesis of leucascandrolide A macrolactone

  摘要：

  Strategies for the stereocontrolled preparations of 2,6-cis- and 2,6-trans-substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in S-E' reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at -78 degrees C yield nonracemic 1,5-diols for chemoselective internal backside displacements. This concept is developed as a flexible and reliable strategy in studies toward leucascandrolide A macrolactone 2 via the sequential applications of S-E' reactions leading to the C-1-C-9 aldehyde 14, and the bis-tetrahydropyran 59, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.020

文献信息

• A Bidirectional S_E′ Strategy for 1,5-<i>syn</i> and 1,5-<i>anti</i> Stereocontrol toward the Synthesis of Complex Polyols
  作者：David R. Williams、Christopher D. Claeboe、Bo Liang、Nicolas Zorn、Nicholas S. C. Chow

  DOI：10.1021/ol3015682

  日期：2012.8.3

  Studies report a bidirectional SE′ strategy applicable for the stereocontrolled synthesis of nonracemic 1,5-syn and 1,5-anti diols and their derivatives. Nonracemic 1,3,2-diazaborolidine auxiliaries are incorporated by chemoselective tin–boron exchange to provide reactive allylic boranes. The convergent pathway utilizes sequential reactions with two aldehydes producing stereochemical outcomes from

  研究报告了一种双向 S E ' 策略，适用于非外消旋 1,5- syn和 1,5- anti二醇及其衍生物的立体控制合成。非外消旋 1,3,2-二氮杂硼烷助剂通过化学选择性锡-硼交换加入，以提供反应性烯丙基硼烷。收敛途径利用与两种醛的顺序反应，分别从循环、闭合和开放过渡态偏好产生立体化学结果。peloruside A片段16的合成分四步完成，由容易获得的醛9和13 组成。
• Formal Synthesis of Leucascandrolide A
  作者：David R. Williams、Scott V. Plummer、Samarjit Patnaik

  DOI：10.1002/anie.200351817

  日期：2003.8.25