(2R,3R,4R)-hept-6-ene-2,3,4-tri-O-acetate | 1197419-49-0

• 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: (2R,3R,4R)-hept-6-ene-2,3,4-tri-O-acetate
• 英文别名: (2R,3R,4R)-hept-6-ene-2,3,4-triyl triacetate；(2R,3R,4R)-hept-6-ene-2,3,4-triol triacetate；[(2R,3R,4R)-3,4-diacetyloxyhept-6-en-2-yl] acetate
• CAS: 1197419-49-0
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: JVACTWUGGKSWPC-BZHVJNSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-hept-6-ene-2,3,4-tri-O-acetate 在 Hoveyda-Grubbs catalyst second generation 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 50.5h， 生成 (2R,3R,4R,8R,E)-8-(acryloyloxy)undeca-6,10-diene-2,3,4-tri-O-acetate
  参考文献：
  名称：

  Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology

  摘要：

  Synargentolide A was synthesized in 11 steps starting from the commercially available 2,2-dimethyl-1,3-dioxan-5-one, employing the SAMP/RAMP-methodology via an alpha,alpha'-bis-alkylation to generate the first two stereogenic centers with virtually complete asymmetric induction (de, ee > 99%). After the asymmetric synthesis of the triol fragment of the molecule, the delta-lactone moiety was constructed using an asymmetric allylation, esterification, and ring-closing metathesis sequence.

  DOI：

  10.1055/s-0032-1316865
• 作为产物：
  描述：

  (4R,6R)-4-allyl-2,2,6-trimethyl-1,3-dioxan-5-one 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (2R,3R,4R)-hept-6-ene-2,3,4-tri-O-acetate
  参考文献：
  名称：

  Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology

  摘要：

  Synargentolide A was synthesized in 11 steps starting from the commercially available 2,2-dimethyl-1,3-dioxan-5-one, employing the SAMP/RAMP-methodology via an alpha,alpha'-bis-alkylation to generate the first two stereogenic centers with virtually complete asymmetric induction (de, ee > 99%). After the asymmetric synthesis of the triol fragment of the molecule, the delta-lactone moiety was constructed using an asymmetric allylation, esterification, and ring-closing metathesis sequence.

  DOI：

  10.1055/s-0032-1316865

文献信息

• First stereoselective synthesis of synargentolide A and revision of absolute stereochemistry
  作者：Gowravaram Sabitha、Peddabuddi Gopal、C. Nagendra Reddy、J.S. Yadav

  DOI：10.1016/j.tetlet.2009.08.109

  日期：2009.11

  The first stereoselective total synthesis of synargentolide A isolated from Syncolostemon argenteus has been achieved from commercially available (R)-benzyl glycidyl ether using Sharpless asymmetric epoxidation and cross-metathesis reactions as the key steps. Comparing the spectral data of the synthesized and naturally occurring synargentolide A, the C4′ and C6′- stereogenic centers of the natural

  从Syncolostemon argenteus分离出的香根草素A的第一个立体选择性全合成已使用Sharpless不对称环氧化和交叉复分解反应为关键步骤，从市售（R）-苄基缩水甘油醚中获得。比较合成的和天然存在的同化内酯A的光谱数据，天然同化内酯A的C4'和C6'-立体中心被分配了校正的反关系。
• An Efficient Stereoselective Total Synthesis of Synargentolide A and Its Epimer
  作者：Biswanath Das、Penagaluri Balasubramanyam、Boyapati Veeranjaneyulu、Gandolla Chinna Reddy

  DOI：10.1002/hlca.201000342

  日期：2011.5

  The stereoselective total synthesis of a naturally occurring α‐pyrone (=2H‐pyran‐2‐one) derivative, synargentolide A (1), and of its epimer 2 (with the originally proposed structure of synargentolide A) was efficiently accomplished involving D‐tartaric acid as the starting material and an olefin cross‐metathesis reaction as the key step.

  有效地完成了涉及D的自然存在的α-吡喃酮（= 2 H-吡喃-2-酮）衍生物synargentolide A（1）及其差向异构体2的立体选择性全合成。酒石酸为起始原料，烯烃交叉复分解反应为关键步骤。
• An efficient synthesis of synargentolide A from d-mannitol
  作者：Ahmed Kamal、Moku Balakrishna、Papagari Venkat Reddy、Shaikh Faazil

  DOI：10.1016/j.tetasy.2010.10.001

  日期：2010.10

  An efficient synthesis of synargentolide A is described by using D-mannitol and D-malic acid The key features of the synthetic strategy include Wittig olefination ring closing-metathesis reaction and cross-metathesis reaction for the formation of synargentolide A (C) 2010 Elsevier Ltd All rights reserved
• ROUSH, W. R.;BROWN, R. J.;DIMARE, M., J. ORG. CHEM., 1983, 48, N 25, 5083-5093
  作者：ROUSH, W. R.、BROWN, R. J.、DIMARE, M.

  DOI：——

  日期：——