(E)-ethyl 4-((4R,5S)-5-((S)-1-hydroxyallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate | 1610954-21-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-ethyl 4-((4R,5S)-5-((S)-1-hydroxyallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate
• 英文别名: ethyl (E)-4-[(4R,5S)-5-[(1S)-1-hydroxyprop-2-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-enoate
• CAS: 1610954-21-6
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: XDDVWXGABKCQDD-QDHWCFKQSA-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：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-((4R,5S)-5-((S)-1-hydroxyallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以72%的产率得到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
• 作为产物：
  描述：

  (E)-ethyl 4-((4R,5R)-5-((S)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(4-thoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate 在 咪唑 、 copper(II) choride dihydrate 、 碘 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 (E)-ethyl 4-((4R,5S)-5-((S)-1-hydroxyallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate
  参考文献：
  名称：

  Stereoselective synthesis of the C-11 to C-19 segment of macrolactin 3 via a center inversion followed by Oxa-Michael addition approach

  摘要：

  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]

  DOI：

  10.1080/07328303.2017.1354012