(2S,3S,4R,5S,6R,7R)-1-benzyloxy-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctane | 236401-62-0

• 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)-1-benzyloxy-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctane
• 英文别名: (4S,5R,6S)-4-[(2R,3R)-3-[(4-methoxyphenyl)methoxy]butan-2-yl]-2,2,5-trimethyl-6-[(2S)-1-phenylmethoxypropan-2-yl]-1,3-dioxane
• CAS: 236401-62-0
• 化学式: C₂₉H₄₂O₅
• 分子量: 470.649
• InChiKey: GRNREBCWJSIZKJ-ORQJLPJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6R,7R)-1-benzyloxy-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctane 在 W-2 Raney nickel 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 (2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al
  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：

  (S)-1-苄氧基-2-甲基戊烷-3-酮 在 氯代二环己基硼烷 、 4-甲基苯磺酸吡啶 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醚 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 63.5h， 生成 (2S,3S,4R,5S,6R,7R)-1-benzyloxy-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctane
  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

文献信息

• Total Synthesis of Elaiolide Using a Copper(I)-Promoted Stille Cyclodimerization Reaction
  作者：Ian Paterson、Henry-Georges Lombart、Charlotte Allerton

  DOI：10.1021/ol990004c

  日期：1999.7.1

  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.