(4S,5S)-4-triisopropylsilyloxy-5-amino-7-methyl-1-octene | 1100345-35-4

• 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: (4S,5S)-4-triisopropylsilyloxy-5-amino-7-methyl-1-octene
• 英文别名: (4S,5S)-2-methyl-5-tri(propan-2-yl)silyloxyoct-7-en-4-amine
• CAS: 1100345-35-4
• 化学式: C₁₈H₃₉NOSi
• 分子量: 313.599
• InChiKey: WDLMHDBDXQDAHB-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-triisopropylsilyloxy-5-amino-7-methyl-1-octene 、 1H-benzotriazole-1-carboxylic acid, 1,1-dimethylethyl ester, 3-oxide 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以90%的产率得到(4S,5S)-4-triisopropylsilyloxy-5-[(tert-butoxycarbonyl)amino]-7-methyl-1-octene
  参考文献：
  名称：

  Strict Reagent Control in the Asymmetric Allylboration of N-TIPS-α-Amino Aldehydes with the B-Allyl-10-TMS-9-borabicyclo[3.3.2]decanes

  摘要：

  The allylboration of enantiomerically pure N-triisopropylsilyl-alpha-amino aldehydes (2) with B-allyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decanes (1) proceeds cleanly at -78 degrees C, exhibiting essentially complete reagent control. After an oxidative workup, an HOAc-mediated N-->O TIPS rearrangement facilitates the clean formation of stable O-TIPS protected beta-amino alcohol derivatives 3 which are isolated in 60-83% yields in >= 96% de and >99% ee. For the leucinal series (R = i-Bu), an efficient entry to either statine (8aSS) or epi-statine (8aRS) is reported illustrating the versatility of this potent 1/2 combination.

  DOI：

  10.1021/ol802685e
• 作为产物：
  描述：

  C₁₈H₃₉NOSi 在 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 72.0h， 以1.04 g的产率得到(4S,5S)-4-triisopropylsilyloxy-5-amino-7-methyl-1-octene
  参考文献：
  名称：

  Strict Reagent Control in the Asymmetric Allylboration of N-TIPS-α-Amino Aldehydes with the B-Allyl-10-TMS-9-borabicyclo[3.3.2]decanes

  摘要：

  The allylboration of enantiomerically pure N-triisopropylsilyl-alpha-amino aldehydes (2) with B-allyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decanes (1) proceeds cleanly at -78 degrees C, exhibiting essentially complete reagent control. After an oxidative workup, an HOAc-mediated N-->O TIPS rearrangement facilitates the clean formation of stable O-TIPS protected beta-amino alcohol derivatives 3 which are isolated in 60-83% yields in >= 96% de and >99% ee. For the leucinal series (R = i-Bu), an efficient entry to either statine (8aSS) or epi-statine (8aRS) is reported illustrating the versatility of this potent 1/2 combination.

  DOI：

  10.1021/ol802685e

文献信息

• Strict Reagent Control in the Asymmetric Allylboration of <i>N</i>-TIPS-α-Amino Aldehydes with the <i>B-</i>Allyl-10-TMS-9-borabicyclo[3.3.2]decanes
  作者：Buddy Soto-Cairoli、John A. Soderquist

  DOI：10.1021/ol802685e

  日期：2009.1.15

  The allylboration of enantiomerically pure N-triisopropylsilyl-alpha-amino aldehydes (2) with B-allyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decanes (1) proceeds cleanly at -78 degrees C, exhibiting essentially complete reagent control. After an oxidative workup, an HOAc-mediated N-->O TIPS rearrangement facilitates the clean formation of stable O-TIPS protected beta-amino alcohol derivatives 3 which are isolated in 60-83% yields in >= 96% de and >99% ee. For the leucinal series (R = i-Bu), an efficient entry to either statine (8aSS) or epi-statine (8aRS) is reported illustrating the versatility of this potent 1/2 combination.