(2R,3R)-3-(diethyl-iso-propylsilyloxy)-2-ethyl-1-butanal | 236401-58-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R)-3-(diethyl-iso-propylsilyloxy)-2-ethyl-1-butanal
• 英文别名: (2R,3R)-3-[diethyl(propan-2-yl)silyl]oxy-2-ethylbutanal
• CAS: 236401-58-4
• 化学式: C₁₃H₂₈O₂Si
• 分子量: 244.45
• InChiKey: HMBPEHWJYBDENK-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-(diethyl-iso-propylsilyloxy)-2-ethyl-1-butanal 、 (3E,5E,11E,13E)-(7S,8S,15S,16S)-8,16-bis((1R,2R,3S)-1,3-dimethyl-4-oxo-2-triethylsilanyloxypentyl)-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以75%的产率得到(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(1R,2R,3S,6R,7S,8R)-8-(diethyl-iso-propylsilyloxy)-7-ethyl-6-hydroxy-4-oxo-2-triethylsilyloxy-1,3-dimethylpentyl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
  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：

  二乙基异丙基氯硅烷 在 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 (2R,3R)-3-(diethyl-iso-propylsilyloxy)-2-ethyl-1-butanal
  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.