Tributyl-(1-methoxy-3-methyl-butyl)-plumbane | 140849-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Tributyl-(1-methoxy-3-methyl-butyl)-plumbane
• CAS: 140849-76-9
• 化学式: C₁₈H₄₀OPb
• 分子量: 479.715
• InChiKey: SMCQHZKGHKKBPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3β-(t-butyldimethylsilyloxy)-23,24-dinorchol-5-enaldehyde 、 Tributyl-(1-methoxy-3-methyl-butyl)-plumbane 在 oxonium 、 四氯化钛 作用下， 生成 (2S,3R,4R)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-4-methoxy-6-methyl-heptan-3-ol
  参考文献：
  名称：

  Stereocontrol of three contiguous chiral centers of brassinosteroid side chain by using .alpha.-alkoxy organoleads

  摘要：

  The reaction of steroidal aldehyde 2 with chiral alpha-methoxyorganolead (S)-3 in the presence of TiCl4 gave the Cram-syn product 4, a precursor of 28-norbrassinolide, in 90% yield as a single stereoisomer. A kinetic resolution was observed in the TiCl4 mediated reaction of 2 with (+/-)-3; again 4 was produced in 99% yield as a single isomer.

  DOI：

  10.1021/jo00037a002

文献信息

• Very high diastereofacial stereoselectivity in the α-methoxy organolead–aldehyde condensation. Stereocontrol of three contiguous chiral centres
  作者：Toshiaki Furuta、Yoshinori Yamamoto

  DOI：10.1039/c39920000863

  日期：——

  The reaction of the α-methoxylead derivative 1a with 2-phenylpropanal in the presence of TiCl4 gave the 1,2-syn-2,3-syn product 2 with very high diastereoselectivity: 1,2-syn/1,2-anti= 95/5 and 2,3-syn/2,3-anti= 100/0.

  在 TiCl4 存在下，δ-甲氧基铅衍生物 1a 与 2-苯基丙醛反应生成 1,2-鞘氨醇-2,3-鞘氨醇产物 2，具有极高的非对映选择性：1,2-鞘氨醇/1,2-反= 95/5，2,3-鞘氨醇/2,3-反= 100/0。
• Stereocontrol of three contiguous chiral centers of brassinosteroid side chain by using .alpha.-alkoxy organoleads
  作者：Toshiaki Furuta、Yoshinori Yamamoto

  DOI：10.1021/jo00037a002

  日期：1992.5

  The reaction of steroidal aldehyde 2 with chiral alpha-methoxyorganolead (S)-3 in the presence of TiCl4 gave the Cram-syn product 4, a precursor of 28-norbrassinolide, in 90% yield as a single stereoisomer. A kinetic resolution was observed in the TiCl4 mediated reaction of 2 with (+/-)-3; again 4 was produced in 99% yield as a single isomer.