(4S,5S)-2,2-dimethyl-4-((S)-oxiran-2-yl)-5-vinyl-1,3-dioxolane | 1293966-31-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S)-2,2-dimethyl-4-((S)-oxiran-2-yl)-5-vinyl-1,3-dioxolane
• 英文别名: (4S,5S)-4-ethenyl-2,2-dimethyl-5-[(2S)-oxiran-2-yl]-1,3-dioxolane
• CAS: 1293966-31-0
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: AKTQXGIWIPHDOK-FXQIFTODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-2,2-dimethyl-4-((S)-oxiran-2-yl)-5-vinyl-1,3-dioxolane 在 copper(l) iodide 、 盐酸羟胺 、 sodium hydride 、 potassium carbonate 、 臭氧 、 正丁胺 、 三氟乙酸 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 48.33h， 生成 (3R,8S,9S,10S)-10-methoxyheptadeca-4,6-diyne-3,8,9-triol
  参考文献：
  名称：

  First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B

  摘要：

  The first total synthesis of the natural product (+)-oploxyne B is achieved. The synthesis has led to the confirmation of absolute stereochemistry of the natural product. The natural product displayed cytotoxic activity with IC50 values varying from 16 to 53 mu M in four cancer cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.020
• 作为产物：
  描述：

  2,3-O-isopropylidene-D-ribose 在 咪唑 、 N-甲基咪唑 、 potassium tert-butylate 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 56.91h， 生成 (4S,5S)-2,2-dimethyl-4-((S)-oxiran-2-yl)-5-vinyl-1,3-dioxolane
  参考文献：
  名称：

  First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B

  摘要：

  The first total synthesis of the natural product (+)-oploxyne B is achieved. The synthesis has led to the confirmation of absolute stereochemistry of the natural product. The natural product displayed cytotoxic activity with IC50 values varying from 16 to 53 mu M in four cancer cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.020

文献信息

• Stereoselective total synthesis and cytotoxic evaluation of C-9 epimers of herbarumin-II and its C-2 epimer
  作者：Lingaiah Maram、C. Ganesh Kumar、Y. Poornachandra、Biswanath Das

  DOI：10.1016/j.tetlet.2015.06.011

  日期：2015.7

  The total synthesis and cytotoxic evaluation of C-9 epimers of herbarumin-II and its C-2 epimer are described for the first time. The key transformations of the synthesis include Wittig olefination, MacMillan α-hydroxylation, Pinnick oxidation, Yamaguchi esterification, and intramolecular ring closing metathesis.

  首次描述了标本蛋白II的C-9差向异构体及其C-2差向异构体的总合成和细胞毒性评估。合成的关键转变包括Wittig烯烃化，MacMillanα-羟基化，Pinnick氧化，Yamaguchi酯化和分子内闭环复分解。
• Synthetic Studies on Lytophilippine A: Synthesis of the Proposed Structure
  作者：Ki Po Jang、Soo Young Choi、Young Keun Chung、Eun Lee

  DOI：10.1021/ol2007296

  日期：2011.5.6

  Synthesis of the proposed structure of lytophilippine A was accomplished employing SmI2-mediated 5-exo cyclization of an aldehydo β-alkoxyvinyl sulfoxide and ring-closing metathesis reaction.

  利用SmI 2介导的醛基β-烷氧基乙烯基亚砜的5-外显环化和闭环易位反应，完成了所建议的冻干果胶A结构的合成。
• A Further Contribution to the Study of Sagittamide A: Synthesis of a Pivotal Intermediate Belonging to a Rare L-Series
  作者：Anne Humbert、Karen Plé、Dominique Harakat、Agathe Martinez、Arnaud Haudrechy

  DOI：10.3390/molecules17077709

  日期：——

  A key saggitamide intermediate corresponding to a rare sugar framework has been obtained. This approach should help to establish the overall configuration of more complex structures of the sagittamide family.

  我们获得了一种与稀有糖框架相对应的关键箭毒酰胺中间体。这种方法有助于确定箭头酰胺家族更复杂结构的整体构型。
• Kuefner, Ulrike; Schmidt, Richard R., Liebigs Annalen der Chemie, 1986, # 9, p. 1600 - 1609
  作者：Kuefner, Ulrike、Schmidt, Richard R.

  DOI：——

  日期：——
• First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B
  作者：P. Srihari、A. Sathish Reddy、J.S. Yadav、D. Yedlapudi、Shasi V. Kalivendi

  DOI：10.1016/j.tetlet.2013.08.020

  日期：2013.10

  The first total synthesis of the natural product (+)-oploxyne B is achieved. The synthesis has led to the confirmation of absolute stereochemistry of the natural product. The natural product displayed cytotoxic activity with IC50 values varying from 16 to 53 mu M in four cancer cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.