(3aS,6S,7aS)-6-heptyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-ol | 1251927-21-5

• 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: (3aS,6S,7aS)-6-heptyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-ol
• 英文别名: (3aS,6S,7aS)-6-heptyl-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-ol
• CAS: 1251927-21-5
• 化学式: C₁₅H₂₈O₄
• 分子量: 272.385
• InChiKey: ICDGBCGBIOLMIG-AIOZOAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,6S,7aS)-6-heptyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 potassium tert-butylate 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.33h， 生成 achaetolide C6,C7-O-acetonide
  参考文献：
  名称：

  The stereoselective total synthesis of (−)-achaetolide

  摘要：

  The stereoselective total synthesis of (-)-achaetolide is described in a convergent manner. Grignard addition, Wittig homologation, acetate aldol and ring closing metathesis reactions were the key steps involved. The required olefinic alcohol fragments were synthesized from a single chiral pool material 2-deoxy-D-ribose and olefinic acid fragment was prepared from acetate aldol reaction. Both the olefinic acid and alcohols were prepared in a concise method. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.010
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 二异丁基氢化铝 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 25.0h， 生成 (3aS,6S,7aS)-6-heptyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-ol
  参考文献：
  名称：

  The stereoselective total synthesis of (−)-achaetolide

  摘要：

  The stereoselective total synthesis of (-)-achaetolide is described in a convergent manner. Grignard addition, Wittig homologation, acetate aldol and ring closing metathesis reactions were the key steps involved. The required olefinic alcohol fragments were synthesized from a single chiral pool material 2-deoxy-D-ribose and olefinic acid fragment was prepared from acetate aldol reaction. Both the olefinic acid and alcohols were prepared in a concise method. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.010

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.