(2S,4S,5S,6S,7R)-1-benzyloxy-5-hydroxy-7-(4-methoxybenzyloxy)-2,4,6-trimethyloctan-3-one | 236401-63-1

• 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,4S,5S,6S,7R)-1-benzyloxy-5-hydroxy-7-(4-methoxybenzyloxy)-2,4,6-trimethyloctan-3-one
• 英文别名: (2S,4S,5S,6S,7R)-5-hydroxy-7-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-1-phenylmethoxyoctan-3-one
• CAS: 236401-63-1
• 化学式: C₂₆H₃₆O₅
• 分子量: 428.569
• InChiKey: DHSHGLDAGCNWFT-DFQPOLAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 草酰氯 、 氢气 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 58.0h， 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：

  (2S,4R,5R)-5-hydroxy-4-methyl-3-oxohexan-2-yl benzoate 在 sodium tetrahydroborate 、 sodium periodate 、 三氟甲磺酸 、 氯代二环己基硼烷 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 32.5h， 生成 (2S,4S,5S,6S,7R)-1-benzyloxy-5-hydroxy-7-(4-methoxybenzyloxy)-2,4,6-trimethyloctan-3-one
  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.