[(3S,4E)-2-methoxy-2-(2-methyl-1-phenylmethoxypropan-2-yl)-4-prop-2-enylideneoxan-3-yl] octanoate | 880343-27-1

• 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: [(3S,4E)-2-methoxy-2-(2-methyl-1-phenylmethoxypropan-2-yl)-4-prop-2-enylideneoxan-3-yl] octanoate
• CAS: 880343-27-1
• 化学式: C₂₈H₄₂O₅
• 分子量: 458.638
• InChiKey: BLZFRFVNCCVWFC-OCRGJCOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3S,4E)-2-methoxy-2-(2-methyl-1-phenylmethoxypropan-2-yl)-4-prop-2-enylideneoxan-3-yl] octanoate 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.83h， 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：

  (4S,5E)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-4-hydroxy-2,2-dimethyl-1-phenylmethoxyocta-5,7-dien-3-one 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 达卡巴嗪 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 [(3S,4E)-2-methoxy-2-(2-methyl-1-phenylmethoxypropan-2-yl)-4-prop-2-enylideneoxan-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

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.