(3S,4S,6S)-6-heptyl-3,4-dihydroxyoxan-2-one | 1251927-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4S,6S)-6-heptyl-3,4-dihydroxyoxan-2-one
• CAS: 1251927-19-1
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: GKENUAUJKLRJJV-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S,6S)-6-heptyl-3,4-dihydroxyoxan-2-one 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以72%的产率得到(3aS,6S,7aS)-6-heptyl-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyran-4(6H)-one
  参考文献：
  名称：

  First total synthesis of achaetolide

  摘要：

  The first total synthesis of achaetolide, a 10-membered macrolactone was achieved using Mitsunobu reaction and Grubbs ring-closing metathesis reaction as the key steps for ring construction. The desired stereo centres were generated by Jacobsen hydrolytic kinetic resolution, dihydroxylation and Sharpless asymmetric epoxidation reactions. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.127
• 作为产物：
  描述：

  (S)-6-Heptyl-5,6-dihydro-pyran-2-one 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 生成 (3S,4S,6S)-6-heptyl-3,4-dihydroxyoxan-2-one
  参考文献：
  名称：

  First total synthesis of achaetolide

  摘要：

  The first total synthesis of achaetolide, a 10-membered macrolactone was achieved using Mitsunobu reaction and Grubbs ring-closing metathesis reaction as the key steps for ring construction. The desired stereo centres were generated by Jacobsen hydrolytic kinetic resolution, dihydroxylation and Sharpless asymmetric epoxidation reactions. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.127

文献信息

• First total synthesis of achaetolide
  作者：S. Chandrasekhar、S.V. Balaji、G. Rajesh

  DOI：10.1016/j.tetlet.2010.07.127

  日期：2010.9

  The first total synthesis of achaetolide, a 10-membered macrolactone was achieved using Mitsunobu reaction and Grubbs ring-closing metathesis reaction as the key steps for ring construction. The desired stereo centres were generated by Jacobsen hydrolytic kinetic resolution, dihydroxylation and Sharpless asymmetric epoxidation reactions. (c) 2010 Elsevier Ltd. All rights reserved.