(2S,3S,4S,5R,E)-7-[(R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]hept-6-ene-2,3,4,5-tetrayl tetraacetate | 110351-37-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S,4S,5R,E)-7-[(R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]hept-6-ene-2,3,4,5-tetrayl tetraacetate
• 英文别名: (6R)-6-[(3R,4S,5S,6S)-3,4,5,6-tetraacetoxyhept-1-enyl]-5,6-dihydropyran-2-one；(+)-anamarine；anamarine；Anamarin；[(E,2S,3S,4S,5R)-3,4,5-triacetyloxy-7-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hept-6-en-2-yl] acetate
• CAS: 110351-37-6；111955-42-1；114883-39-5；73413-69-1
• 化学式: C₂₀H₂₆O₁₀
• 分子量: 426.42
• InChiKey: IIGKKKGWVQSBLY-HCHVBTQVSA-N

物化性质

• 沸点：
  523.8±50.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  D-(-)-古洛糖酸-gamma-内酯 在 aluminum oxide 、 正丁基锂 、 potassium tert-butylate 、 sodium acetate 、 phosphorus pentoxide 、 镍 、 二苯二硫醚 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 六甲基磷酰三胺 、 乙醚 、 乙醇 、 水 、 丙酮 、 苯 为溶剂， 反应 20.0h， 生成 (2S,3S,4S,5R,E)-7-[(R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]hept-6-ene-2,3,4,5-tetrayl tetraacetate
  参考文献：
  名称：

  A convergent total synthesis of (+)-anamarine from (R,R)-tartrate and D-gulonolactone

  摘要：

  DOI：

  10.1016/s0040-4039(00)96881-3

文献信息

• Stereoselective Total Synthesis of (+)-Anamarine and 8-epi-(–)-Anamarine from d-Mannitol
  作者：Rajender Karnekanti、Marumamula Hanumaiah、Gangavaram Sharma

  DOI：10.1055/s-0034-1380864

  日期：——

  products. Stereoselective total synthesis of (+)-anamarine and the first synthesis of 8-epi-(–)-anamarine, its nonnatural diastereomer, were achieved from readily available d-mannitol. The key reactions involved were asymmetric dihydroxylation, cross-metathesis and ring-closing metathesis reactions. The approach is adoptable advantageously for the diversity-oriented synthesis of several related classes

  摘要 立体选择性的全合成（+）-橘红和第一个合成的8- Epi -（-）-橘红是其非天然非对映异构体，是从现成的d-甘露醇中获得的。涉及的关键反应是不对称二羟基化，交叉复分解和闭环复分解反应。该方法有利地可用于几种相关类别的天然产物的面向多样性的合成。 立体选择性的全合成（+）-橘红和第一个合成的8- Epi -（-）-橘红是其非天然非对映异构体，是从现成的d-甘露醇中获得的。涉及的关键反应是不对称二羟基化，交叉复分解和闭环复分解反应。该方法有利地可用于几种相关类别的天然产物的面向多样性的合成。
• Total synthesis of (+)-anamarine
  作者：Krishnammagari Suresh Kumar、Cirandur Suresh Reddy

  DOI：10.1039/c2ob06940g

  日期：——

  Total synthesis of (+)-anamarine a polyoxygenated δ-pyranone natural product was accomplished via cross-metathesis protocol starting from 3-butene-1-ol and glycidol. Other key features of this synthetic strategy include use of Sharpless asymmetric epoxidation, dihydroxylation, and deoxygenation-isomerization through allene rearrangement.

  (+)-安玛琳的全合成是一种多氧化的δ-吡喃酮天然产品，采用交叉美克斯法从3-丁烯-1-醇和环氧醇出发实现。该合成策略的其他关键特点包括使用Sharpless不对称环氧化、二羟基化以及通过全烯重排进行去氧化-异构化。
• Stereoselective synthesis of anamarine
  作者：Santiago Dı́az-Oltra、Juan Murga、Eva Falomir、Miguel Carda、J.Alberto Marco

  DOI：10.1016/j.tet.2004.02.003

  日期：2004.3

  A stereoselective synthesis of the naturally occurring, α,β-unsaturated lactone anamarine is described. The key step was a highly stereoselective aldol reaction of a protected erythrulose derivative with a chiral aldehyde. Another relevant step was an asymmetric aldehyde allylation with a chiral allylborane. The lactone ring was made by means of a ring-closing metathesis.

  描述了天然存在的α，β-不饱和内酯阿马林的立体选择性合成。关键步骤是受保护的赤藓糖衍生物与手性醛的高度立体选择性醛醇缩合反应。另一个相关步骤是与手性烯丙基硼烷的不对称醛烯丙基化。内酯环通过闭环复分解反应制得。
• De Novo Asymmetric Synthesis of Anamarine and Its Analogues
  作者：Dong Gao、George A. O'Doherty

  DOI：10.1021/jo051681p

  日期：2005.11.1

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.
• Stereoselective total synthesis of (+)-anamarine via cross-metathesis protocol
  作者：Gowravaram Sabitha、C. Nagendra Reddy、Peddabuddi Gopal、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.08.077

  日期：2010.10

  A convergent stereoselective total synthesis of (+)-anamarine via cross-metathesis (CM) protocol starting from 2-butyn-1,4-diol and vinyl lactone is reported. Other key features of the strategy include the use of Sharpless asymmetric epoxidation, Sharpless dihydroxylation, and Red-Al reduction. (C) 2010 Elsevier Ltd. All rights reserved.