((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate | 121469-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate
• CAS: 121469-49-6
• 化学式: C₁₅H₂₀O₅S
• 分子量: 312.387
• InChiKey: DMUNLDYFGILRRO-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate 在 二异丁基氢化铝 、 sodium iodide 作用下， 以 正己烷 、 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  Bhunia, Nisith; Das, Biswanath, Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1633 - 1642

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S,5S)-4,5-Bis-ethoxymethyl-2,2-dimethyl-[1,3]dioxolane 在 正丁基锂 、 草酰氯 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 mineral oil 为溶剂， 反应 7.08h， 生成 ((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Bhunia, Nisith; Das, Biswanath, Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1633 - 1642

  摘要：

  DOI：

文献信息

• Tandem Ring-Closing/Cross-Metathesis Approach for the Synthesis of Synargentolide B and Its Stereoisomers
  作者：Gowravaram Sabitha、Kontham Shankaraiah、Jhillu S. Yadav

  DOI：10.1002/ejoc.201300434

  日期：2013.8

  stereoisomers have been accomplished from L-(+)- and D-(–)-diethyl tartrates, D-ribose, and D-mannitol as chiral pool starting materials. The key step was a tandem ring-closing/cross-metathesis reaction in which lactone formation and fragment coupling were accomplished in one pot. The spectroscopic data of synthetic product 2c were in agreement with those reported for the natural product. Synargentolide

  以 L-(+)- 和 D-(-)-酒石酸二乙酯、D-核糖和 D-甘露醇为手性池起始材料，已完成了合成内酯 B 及其三种立体异构体的立体选择性合成。关键步骤是串联闭环/交叉复分解反应，其中内酯形成和片段偶联在一锅中完成。合成产物 2c 的光谱数据与天然产物报道的数据一致。由 Rivett 等人分离的 Synargentolide B。和 Pereda-Miranda 等人分离的化合物。不是非对映异构体，而是相同的。
• Synthesis of Side-Chain Unsaturated<i>endo</i>- and<i>exo</i>-Brevicomins. Representatives of Pheromone Analogs in the Dioxabicyclo[3.2.1]octane Series
  作者：Stefan Wershofen、H. -D. Scharf

  DOI：10.1055/s-1988-27729

  日期：——

  The title substances endo- and exo-9 were synthesized via selective trans- and cis-opening of the epoxy tosylate 3, respectively. The tosylate 3 is easily obtainable from pentadienol 1.

  标题化合物内-和外-9是通过选择性反式和顺式开环环氧托烷基酯3合成的。托烷基酯3可以容易地从五炔醇1获得。
• Asymmetric sharpless epoxidation of divinylcarbinol. Erythro-D- and -L-4-pentenitols by hydrolysis of regioisomeric epoxy-4-pentenols
  作者：Volker Jäger、Detlef Schröter、Bernhard Koppenhoefer

  DOI：10.1016/s0040-4020(01)96130-7

  日期：——

  The asymmetric Sharpless epoxidation of divinylcarbinol (1), a secondary, achiral allylic alcohol, is described in detail. The epoxidation proceeds with high enantio-control and diastereo-selection. The resulting 1,2-epoxy-4-pentene-3-ols 2 are equilibrated to afford the internal epoxides 5. Hydrolysis of the regioisomers 2 and 5, respectively, furnishes opposite enantiomers of erythro-4-pentenitols

  详细描述了仲乙烯基非手性烯丙醇二乙烯基甲醇（1）的不对称Sharpless环氧化反应。环氧化以高对映体控制和非对映选择进行。使所得的1，2-环氧-4-戊烯-3-醇2平衡以提供内部环氧化物5。区域异构体2和5的水解分别以高选择性提供了赤型-4-戊烯醇3的相反对映异构体。描述了3的几种衍生物，以及较少的立体选择性路线的结果-来自D-甘油醛丙酮化物（10）-提供了苏氨酸的NMR数据系列。-报告了二乙烯基甲醇（1）的急性毒性，以及通过Ames试验确定的1，L- 2和L- 5的致突变性。
• Development of Chiral Terminal-Alkene−Phosphine Hybrid Ligands for Palladium-Catalyzed Asymmetric Allylic Substitutions
  作者：Zhaoqun Liu、Haifeng Du

  DOI：10.1021/ol101069y

  日期：2010.7.2

  A variety of novel chiral terminal-alkene phosphine hybrid ligands were successfully developed from diethyl L-tartrate for palladium-catalyzed asymmetric allylic alkylations, etherifications, and amination to give the desired products in excellent yields and ee's.
• Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives
  作者：Chisato Mukai、Jin Sung Kim、Hiroshi Sonobe、Miyoji Hanaoka

  DOI：10.1021/jo990819z

  日期：1999.9.1

  Treatment of (5S,6S)-5,6-bis(tert-butyldimethylsiloxy)-8-(substituted)oct-1-en-7-yne derivatives, prepared from diethyl L-tartrate, with Co-2(CO)(8) afforded the corresponding cobalt-complexed enynes, which were subsequently exposed to the typical Pauson-Khand conditions to furnish highly stereoselectively or exclusively (2S,3S,6S)-2,3-bis(tert-butyldimetbylsiloxy)-9-(substituted)bicyclo[4.3.0]non-1(9)-en-8-ones. On the other hand, (3S,4S)-1-(substituted)oct-7-en-1-yne-3,4-diol congeners produced, on exposure to the Pauson-Khand conditions, (2S,3S,6R)-2,3-dihydroxy-9-(substituted) bicyclo[4.3.0]-non-1(9)-en-8-one derivatives in a highly stereoselective manner. The newly developed procedure has been shown to be useful for construction of the 2,3-bis(oxygenated)-7-(substituted)-bicyclo[4.3.0]non-6-en-8-one framework in a stereocomplementary as well as stereoselective fashion.