(3S,4R,5S,6S)-6-hydroxy-3,5-dimethyl-9-(tributylstannyl)non-8-en-4-yl (E)-cinnamate | 1362849-41-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (3S,4R,5S,6S)-6-hydroxy-3,5-dimethyl-9-(tributylstannyl)non-8-en-4-yl (E)-cinnamate
• 英文别名: [(E,3S,4R,5S,6S)-6-hydroxy-3,5-dimethyl-9-tributylstannylnon-8-en-4-yl] (E)-3-phenylprop-2-enoate
• CAS: 1362849-41-9
• 化学式: C₃₂H₅₄O₃Sn
• 分子量: 605.489
• InChiKey: HIOHJQIJLHSTML-NUGKABRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.99
• 重原子数：
  36
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6S)-6-hydroxy-3,5-dimethyl-9-(tributylstannyl)non-8-en-4-yl (E)-cinnamate 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到(3S,4R,5S,6S)-6-hydroxy-3,5-dimethylnon-8-en-4-yl (E)-cinnamate
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Basiliskamide A

  摘要：

  Basiliskamide A is an antifungal polyketide natural product isolated by Andersen and co-workers from a Bacillus laterosporus isolate, PNG-276. A nine-step enantioselective synthesis of (-)-basiliskamide A is reported, starting from commercially available beta-hydroxy ester 7. The synthesis features a highly diastereoselective mismatched double asymmetric delta-stannylallylboration reaction of aldehyde 5 with the bifunctional allylborane reagent 4.

  DOI：

  10.1021/ol300282e

文献信息

• Enantioselective Synthesis of (−)-Basiliskamide A
  作者：Ming Chen、William R. Roush

  DOI：10.1021/ol300282e

  日期：2012.3.16

  Basiliskamide A is an antifungal polyketide natural product isolated by Andersen and co-workers from a Bacillus laterosporus isolate, PNG-276. A nine-step enantioselective synthesis of (-)-basiliskamide A is reported, starting from commercially available beta-hydroxy ester 7. The synthesis features a highly diastereoselective mismatched double asymmetric delta-stannylallylboration reaction of aldehyde 5 with the bifunctional allylborane reagent 4.