ethyl 2-((3aR,4S,7aR)-2,2-dimethyl-4-vinyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)acetate | 1610954-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: ethyl 2-((3aR,4S,7aR)-2,2-dimethyl-4-vinyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)acetate
• 英文别名: ethyl 2-((3aR,4S,6S,7aR)-2,2-dimethyl-4-vinyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)acetate；ethyl 2-[(3aR,4S,6R,7aR)-4-ethenyl-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]acetate
• CAS: 1610954-20-5
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: DIGJLGDDBWOVNL-XZUYRWCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol 在 咪唑 、 titanium(IV) isopropylate 、 甲醇 、 叔丁基过氧化氢 、 草酰氯 、 L-(+)-酒石酸二异丙酯 、 potassium tert-butylate 、 四丁基氟化铵 、 水 、 碘 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 二正丁基氧化锡 、 potassium carbonate 、 D-(-)-酒石酸二异丙酯 、 氟化氢吡啶 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 50.0h， 生成 ethyl 2-((3aR,4S,7aR)-2,2-dimethyl-4-vinyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)acetate
  参考文献：
  名称：

  Regioselective nucleophilic ring-opening reaction of chiral epoxyallyl alcohols: a ready access to the pyran core of macrolactin 3

  摘要：

  Herein we report the synthetic strategy towards the pyran core of macrolactin 3 via Sharpless epoxidation, titanium(IV) mediated regioselective ring-opening reaction of epoxyallyl alcohol/epoxy alcohol and oxa-Michael addition as the key steps. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.068

文献信息

• Stereoselective synthesis of the C-11 to C-19 segment of macrolactin 3 <i>via</i> a center inversion followed by Oxa-Michael addition approach
  作者：Prashanth Thodupunuri、Marumamula Hanumaiah、Shobanbabu Bommagani、Gangavaram V. M. Sharma

  DOI：10.1080/07328303.2017.1354012

  日期：2017.3.24

  An efficient and short stereoselective synthesis of C11-C19 fragment of Macrolactin 3 was achieved. The vic-triol moiety (C15-C17) was derived from the C2-C4 chiral centers of D-mannose. The C-1 of D-mannose was utilized for the Wittig-olefination followed by hydroxylation using hydroboration reaction to introduce C11-C13 carbon chain in the C11-C19 fragment, whereas C5-C6 carbon chain of mannose was converted into C18-C19 of the target by dehydration reactions. Thus, the main strategy was (a) two consecutive Wittig-olefination reactions on C1 carbon of mannose, (b) inversion of C4 stereocenter, and (c) dehydration of C5-C6 vic-diol to olefin to result in the C11-C19 fragment.[GRAPHICS]
• Regioselective nucleophilic ring-opening reaction of chiral epoxyallyl alcohols: a ready access to the pyran core of macrolactin 3
  作者：Palakodety Radha Krishna、Rajesh Nomula、Kallaganti V.S. Rama Krishna

  DOI：10.1016/j.tetlet.2014.04.068

  日期：2014.5

  Herein we report the synthetic strategy towards the pyran core of macrolactin 3 via Sharpless epoxidation, titanium(IV) mediated regioselective ring-opening reaction of epoxyallyl alcohol/epoxy alcohol and oxa-Michael addition as the key steps. (C) 2014 Elsevier Ltd. All rights reserved.