(1E,4S,5R,6R,7S)-1-iodo-5,7-dimethyl-4-[(2E)-3-phenylacryloxy]-6-methoxymethoxy-oct-1-ene | 781642-44-2

• 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: (1E,4S,5R,6R,7S)-1-iodo-5,7-dimethyl-4-[(2E)-3-phenylacryloxy]-6-methoxymethoxy-oct-1-ene
• 英文别名: [(E,4S,5S,6R,7S)-1-iodo-6-(methoxymethoxy)-5,7-dimethylnon-1-en-4-yl] (E)-3-phenylprop-2-enoate
• CAS: 781642-44-2
• 化学式: C₂₂H₃₁IO₄
• 分子量: 486.39
• InChiKey: UYZDJUOLDMFCAU-GBCAYYAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1E,4S,5R,6R,7S)-1-iodo-5,7-dimethyl-4-[(2E)-3-phenylacryloxy]-6-methoxymethoxy-oct-1-ene 在 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 以69%的产率得到(1E,4S,5R,6R,7S)-5,7-dimethyl-1-iodo-4-[(2E)-3-phenylacryloxy]-oct-1-en-6-ol
  参考文献：
  名称：

  Total Synthesis of Basiliskamides A and B

  摘要：

  The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).

  DOI：

  10.1021/ol048574m
• 作为产物：
  描述：

  (3S,4R,5R,6S)-4,6-dimethyl-5-methoxymethoxy-3-(triisopropylsilyloxy)-octan-1-ol 在 吡啶 、 chromium dichloride 、 4-二甲氨基吡啶 、 草酰氯 、 氢氟酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 184.0h， 生成 (1E,4S,5R,6R,7S)-1-iodo-5,7-dimethyl-4-[(2E)-3-phenylacryloxy]-6-methoxymethoxy-oct-1-ene
  参考文献：
  名称：

  Total Synthesis of Basiliskamides A and B

  摘要：

  The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).

  DOI：

  10.1021/ol048574m

文献信息

• Stereoselective synthesis of basiliskamides A and B via Prins cyclisation
  作者：J.S. Yadav、P. Purushothama Rao、M. Sridhar Reddy、A.R. Prasad

  DOI：10.1016/j.tetlet.2008.07.024

  日期：2008.9

  A stereoselective and convergent approach to basiliskamides A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion, Takai olefination and Stille coupling along with Prins cyclisation. (c) 2008 Elsevier Ltd. All Fights reserved.