(2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-2,7-dihydroxy-4-methoxymethoxy-3,5-dimethyl-heptanoic acid methyl ester | 235791-67-0

• 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: (2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-2,7-dihydroxy-4-methoxymethoxy-3,5-dimethyl-heptanoic acid methyl ester
• CAS: 235791-67-0
• 化学式: C₂₀H₃₂O₈
• 分子量: 400.469
• InChiKey: SOIJFGUMZTVXEW-YRGVVPAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  28.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  103.68
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-2,7-dihydroxy-4-methoxymethoxy-3,5-dimethyl-heptanoic acid methyl ester 在 palladium dihydroxide sodium periodate 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.5h， 生成 (3R,4R,5R)-5-((S)-1-[1,3]dithian-2-yl-ethyl)-3-hydroxy-4-methyldihydro-furan-2-one
  参考文献：
  名称：

  Total Synthesis of Bafilomycin A₁ Relying on Iterative 1,2-Induction in Acyclic Precursors

  摘要：

  The macrolide bafilomycin A(1) was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A(1) via a conventional carbodiimide-mediated Keck-type macrolactonization.

  DOI：

  10.1021/ja011452u
• 作为产物：
  描述：

  (2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以95%的产率得到(2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-2,7-dihydroxy-4-methoxymethoxy-3,5-dimethyl-heptanoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of Bafilomycin A₁ Relying on Iterative 1,2-Induction in Acyclic Precursors

  摘要：

  The macrolide bafilomycin A(1) was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A(1) via a conventional carbodiimide-mediated Keck-type macrolactonization.

  DOI：

  10.1021/ja011452u

文献信息

• Stereocontrolled solution and solid phase enolate alkylations and hydroxylations — generation of three and four contiguous stereogenic carbon atoms in acyclic systems
  作者：Stephen Hanessian、Jianguo Ma、Wengui Wang

  DOI：10.1016/s0040-4039(99)00782-0

  日期：1999.6

  Potassium enolates of gamma-alkoxy-alpha-methyl pentanoates can be alkylated with allylic and benzylic halides in solution and on solid phase with high 2,3-syn selectivity. Polypropionate units can be constructed on solid phase by a series of stereocontrolled conjugate additions and enolate hydroxylations relying on 1,2-induction. (C) 1999 Elsevier Science Ltd. All rights reserved.