Octanoic acid (E)-(S)-1-(3-benzyloxy-2,2-dimethyl-propionyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-penta-2,4-dienyl ester | 880343-26-0

• 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: Octanoic acid (E)-(S)-1-(3-benzyloxy-2,2-dimethyl-propionyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-penta-2,4-dienyl ester
• 英文别名: [(4S,5E)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-2,2-dimethyl-3-oxo-1-phenylmethoxyocta-5,7-dien-4-yl] octanoate
• CAS: 880343-26-0
• 化学式: C₃₃H₅₄O₅Si
• 分子量: 558.874
• InChiKey: AAPKJTQKWSJILE-XGLKJEJJSA-N

物化性质

• 沸点：
  596.6±50.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  39
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Octanoic acid (E)-(S)-1-(3-benzyloxy-2,2-dimethyl-propionyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-penta-2,4-dienyl ester 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 17.83h， 生成 [(3S,4E)-4-(2-hydroxyethylidene)-2-methoxy-2-(2-methyl-1-phenylmethoxypropan-2-yl)oxan-3-yl] octanoate
  参考文献：
  名称：

  Enantioselective Reductive Coupling of Alkynes and α-Keto Aldehydes via Rhodium-Catalyzed Hydrogenation:  An Approach to Bryostatin Substructures

  摘要：

  Hydrogen-mediated reductive coupling of glyoxal 2 and 1,3-enyne 3 provides (x-hydroxy ketone 4 in 70% yield and 91% enantiomeric excess. Notably, the benzylic ether and diene side chain of 4 remain intact under the conditions of hydrogen-mediated coupling. In four steps, alpha-hydroxy ketone 4 is converted to pyrans 8 and 9, which embody key structural features of the bryostatin recognition domain.

  DOI：

  10.1021/ol052976s
• 作为产物：
  描述：

  tert-butyl(hex-5-en-3-yn-1-yloxy)dimethylsilane 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 4-二甲氨基吡啶 、 (R)-2,2'-bis[bis(3-methylphenyl)phosphino]-1,1'-binaphthyl 、 三苯基乙酸 、 氢气 、 达卡巴嗪 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 25.0~65.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 Octanoic acid (E)-(S)-1-(3-benzyloxy-2,2-dimethyl-propionyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-penta-2,4-dienyl ester
  参考文献：
  名称：

  Enantioselective Reductive Coupling of Alkynes and α-Keto Aldehydes via Rhodium-Catalyzed Hydrogenation:  An Approach to Bryostatin Substructures

  摘要：

  Hydrogen-mediated reductive coupling of glyoxal 2 and 1,3-enyne 3 provides (x-hydroxy ketone 4 in 70% yield and 91% enantiomeric excess. Notably, the benzylic ether and diene side chain of 4 remain intact under the conditions of hydrogen-mediated coupling. In four steps, alpha-hydroxy ketone 4 is converted to pyrans 8 and 9, which embody key structural features of the bryostatin recognition domain.

  DOI：

  10.1021/ol052976s

文献信息

• Enantioselective Reductive Coupling of Alkynes and α-Keto Aldehydes via Rhodium-Catalyzed Hydrogenation:  An Approach to Bryostatin Substructures
  作者：Chang-Woo Cho、Michael J. Krische

  DOI：10.1021/ol052976s

  日期：2006.3.2

  Hydrogen-mediated reductive coupling of glyoxal 2 and 1,3-enyne 3 provides (x-hydroxy ketone 4 in 70% yield and 91% enantiomeric excess. Notably, the benzylic ether and diene side chain of 4 remain intact under the conditions of hydrogen-mediated coupling. In four steps, alpha-hydroxy ketone 4 is converted to pyrans 8 and 9, which embody key structural features of the bryostatin recognition domain.