tert-butyl-[(2S,3R,4R)-2,4-dimethyl-1-phenylmethoxyhex-5-en-3-yl]oxy-dimethylsilane | 474095-64-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl-[(2S,3R,4R)-2,4-dimethyl-1-phenylmethoxyhex-5-en-3-yl]oxy-dimethylsilane
• CAS: 474095-64-2
• 化学式: C₂₁H₃₆O₂Si
• 分子量: 348.601
• InChiKey: YXSOCMQYZBWTPX-WSTZPKSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(2S,3R,4R)-2,4-dimethyl-1-phenylmethoxyhex-5-en-3-yl]oxy-dimethylsilane 在 palladium dihydroxide 盐酸 、 ruthenium trichloride 、 sodium periodate 、 四氧化锇 、 锂硼氢 、 氢气 、 N-甲基吗啉氧化物 、 高碘酸 作用下， 以 甲醇 为溶剂， 20.0~25.0 ℃ 、303.98 kPa 条件下， 反应 65.25h， 生成 (2S,3R,4R)-2,4,6-trimethylheptane-1,3-diol
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid and determination of the absolute stereochemistry of the natural product from callipeltin A

  摘要：

  A revised stereostructure of 3-hydroxy-2,4,6-trimethylheptanoic acid, the beta-hydroxy acid that acylates the N-terminus of callipeltin A. is proposed on the basis of analysis of J-coupling in the H-1 NMR spectrum of the acetonide derivative obtained front the acid hydrolysate of callipeltin A. The proposed Structure was definitively confirmed by enantioselective synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00328-2
• 作为产物：
  描述：

  methyl (S)-3-benzyloxy-2-methylpropanoate 在 (+)-Ipc₂BOMe 、 锂硼氢 、 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 tert-butyl-[(2S,3R,4R)-2,4-dimethyl-1-phenylmethoxyhex-5-en-3-yl]oxy-dimethylsilane
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid and determination of the absolute stereochemistry of the natural product from callipeltin A

  摘要：

  A revised stereostructure of 3-hydroxy-2,4,6-trimethylheptanoic acid, the beta-hydroxy acid that acylates the N-terminus of callipeltin A. is proposed on the basis of analysis of J-coupling in the H-1 NMR spectrum of the acetonide derivative obtained front the acid hydrolysate of callipeltin A. The proposed Structure was definitively confirmed by enantioselective synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00328-2

文献信息

• A total synthesis of (.+-.)-tirandamycin B
  作者：Stephen J. Shimshock、Robert E. Waltermire、Philip DeShong

  DOI：10.1021/ja00023a029

  日期：1991.11

  The total synthesis of the dienoyl tetramic acid antibiotic (+/-)-tirandamycin B is described. The key transformations of the strategy include (1) cyclization of pyranone 14 with fluorosilicic acid to provide the 2,6-dioxabicyclo[3.3.1]nonane system of the natural product, (2) reductive removal of the benzyl ether from enone 15, and (3) attachment of the tetramic acid moiety by using the Schlessinger phosphonate protocol. Protection of the primary hydroxyl function of tirandamycin B as the triisopropylsilyl (TIPS) ether was crucial to the success of the strategy.