(2S,3S,4R,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-ol | 236401-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4R,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-ol
• CAS: 236401-70-0
• 化学式: C₂₂H₃₆O₅
• 分子量: 380.525
• InChiKey: XWXWHWSWUKZEAS-GLDUVZCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-ol 在 chromium dichloride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (1E,3S,4S,5R,6S,7R,8R)-1-iodo-8-(4-methoxybenzyloxy)-4,6-isopropylidenedioxy-3,5,7-trimethylnon-1-ene
  参考文献：
  名称：

  Total Synthesis of Elaiolide Using a Copper(I)-Promoted Stille Cyclodimerization Reaction

  摘要：

  The 16-membered macrodiolide elaiolide (2) has been prepared in 20 steps from the ketone (S)-8 in 9.3% overall yield with a diastereoselectivity of 76%, Key steps included the copper(I) thiophene-2-carboxylate promoted cyclodimerization of the vinyl stannane 3 to give the C-2-symmetric macrocycle 16 in 80% yield and the two directional aldol coupling of the macrocyclic diketone 17 with aldehyde 5. Most of the stereocenters in the macrocyclic precursor 3 were constructed using boron aldol methodology developed in this laboratory.

  DOI：

  10.1021/ol990004c
• 作为产物：
  描述：

  (2S,4S,5S,6S,7R)-1-benzyloxy-5-hydroxy-7-(4-methoxybenzyloxy)-2,4,6-trimethyloctan-3-one 在 W-2 Raney nickel 氢气 、 4-甲基苯磺酸吡啶 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 56.5h， 生成 (2S,3S,4R,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-ol
  参考文献：
  名称：

  Total Synthesis of Elaiolide Using a Copper(I)-Promoted Stille Cyclodimerization Reaction

  摘要：

  The 16-membered macrodiolide elaiolide (2) has been prepared in 20 steps from the ketone (S)-8 in 9.3% overall yield with a diastereoselectivity of 76%, Key steps included the copper(I) thiophene-2-carboxylate promoted cyclodimerization of the vinyl stannane 3 to give the C-2-symmetric macrocycle 16 in 80% yield and the two directional aldol coupling of the macrocyclic diketone 17 with aldehyde 5. Most of the stereocenters in the macrocyclic precursor 3 were constructed using boron aldol methodology developed in this laboratory.

  DOI：

  10.1021/ol990004c