(S)-tert-butyl 2-((E)-((4aR,5R,6S,8aS)-6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,8a-dimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyleneamino)-3,3-dimethylbutanoate | 926028-69-5

• 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: (S)-tert-butyl 2-((E)-((4aR,5R,6S,8aS)-6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,8a-dimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyleneamino)-3,3-dimethylbutanoate
• CAS: 926028-69-5
• 化学式: C₃₆H₆₉NO₄Si₂
• 分子量: 636.119
• InChiKey: DALIIPUFIIQFEJ-CSJRJDLBSA-N

物化性质

• 沸点：
  584.6±50.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.37
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.12
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2-((E)-((4aR,5R,6S,8aS)-6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,8a-dimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyleneamino)-3,3-dimethylbutanoate 在 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.75h， 生成
  参考文献：
  名称：

  Development of a Scalable Synthesis of a Common Eastern Tricyclic Lactone for Construction of the Nodulisporic Acids

  摘要：

  A scalable, second-generation synthesis of the densely functionalized eastern tricyclic lactone (+)-6, a common intermediate, for construction of the nodulisporic acids has been achieved. Modifications to the first-generation route now permit access to (+)-6 in 17 steps with an overall 16.5% yield. Key carbon-carbon bond constructions include a Kirk-Petrow (phenylthio)methylation, a Sc(OTf)(3)-catalyzed hydroxymethylation, a Stille carbonylation, and a Koga three-component, conjugate addition-alkylation sequence.

  DOI：

  10.1021/op060204l
• 作为产物：
  描述：

  Spiro[1,3-dioxolane-2,1'(2'H)-naphthalene], 3',4',4'a,7',8',8'a-hexahydro-5',8'a-dimethyl-6'-[(trimethylsilyl)oxy]-, (4'aS,8'aS)- 在 2,6-二甲基吡啶 、 盐酸 、 lithium chloride 、 lithium hexamethyldisilazane 、 tetramethylammonium triacetoxyborohydride 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 、 乙腈 为溶剂， -78.0~140.0 ℃ 、4.67 kPa 条件下， 反应 20.33h， 生成 (S)-tert-butyl 2-((E)-((4aR,5R,6S,8aS)-6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,8a-dimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyleneamino)-3,3-dimethylbutanoate
  参考文献：
  名称：

  Development of a Scalable Synthesis of a Common Eastern Tricyclic Lactone for Construction of the Nodulisporic Acids

  摘要：

  A scalable, second-generation synthesis of the densely functionalized eastern tricyclic lactone (+)-6, a common intermediate, for construction of the nodulisporic acids has been achieved. Modifications to the first-generation route now permit access to (+)-6 in 17 steps with an overall 16.5% yield. Key carbon-carbon bond constructions include a Kirk-Petrow (phenylthio)methylation, a Sc(OTf)(3)-catalyzed hydroxymethylation, a Stille carbonylation, and a Koga three-component, conjugate addition-alkylation sequence.

  DOI：

  10.1021/op060204l

文献信息

• Nodulisporic Acid A Synthetic Studies. 2. Construction of an Eastern Hemisphere Subtarget
  作者：Amos B. Smith、Young Shin Cho、Haruaki Ishiyama

  DOI：10.1021/ol016888t

  日期：2001.11.1

  In this, the second of two Letters, we describe an effective assembly of (+)-4, an eastern hemisphere subtarget comprising the FGH rings of (+)-nodulisporic acid A (1) (17 steps, 9% overall yield). Central to the synthesis is a Koga three-component conjugate addition-alkylation sequence which secures the trans orientation of the vicinal quaternary methyl groups. [reaction: see text]

  在本文中，这是两个字母的第二个字母，我们描述了（+）-4的有效组装，这是一个包含（+）-去甲孢子酸A（1）的FGH环的东半球子目标（17个步骤，总产率为9％）。合成的中心是Koga三组分共轭加成烷基化序列，可确保邻位季甲基的反式定位。[反应：看文字]