(2R,3S,4S)-3-(tert-butyldimethylsilanyloxy)-5-hydroxy-2,4-dimethylhexananoic acid methoxymethyl amide | 397331-46-3

• 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: (2R,3S,4S)-3-(tert-butyldimethylsilanyloxy)-5-hydroxy-2,4-dimethylhexananoic acid methoxymethyl amide
• 英文别名: (2R,3S,4S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-N-methoxy-N,2,4-trimethyl-hexanamide；(2R,3S,4S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-5-hydroxy-N-methoxy-N,2,4-trimethylhexanamide；(2R,3S,4S)-3-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-N-methoxy-N,2,4-trimethylhexanamide
• CAS: 397331-46-3
• 化学式: C₁₆H₃₅NO₄Si
• 分子量: 333.544
• InChiKey: LMPPEHJTMYUSFC-PIGZVRMJSA-N

物化性质

• 沸点：
  374.8±52.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-3-(tert-butyldimethylsilanyloxy)-5-hydroxy-2,4-dimethylhexananoic acid methoxymethyl amide 在 三乙胺 、 三氧化硫吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 以1.1 g的产率得到(2R,3S,4R)-3-(tert-butyldimethylsilanyloxy)-2,4-dimethyl-5-oxohexanoic acid methoxymethylamide
  参考文献：
  名称：

  A Formal Synthesis of (+)-Discodermolide

  摘要：

  Herein, we report the formal synthesis of (+)-discodermolide (1), a promising anticancer agent of sponge origin, in 24 linear steps, with 35 steps in total. The route proceeds from lactone 2, a building block containing the common 1,2-anti-2,3-syn stereotriad found in each of the three subunits, methyl ketone 4 (C-1-C-6), vinyl iodide 7 (C-9--C-14), and iodide 8 (C-15-C-24) utilized for the construction of L The key fragment union was achieved by a Suzuki cross-coupling between 7 and 8.

  DOI：

  10.1021/op049807s
• 作为产物：
  描述：

  (2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide 在 2,6-二甲基吡啶 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 palladium on carbon 、 氢气 作用下， 以 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， -20.0~20.0 ℃ 、900.02 kPa 条件下， 反应 1.83h， 生成 (2R,3S,4S)-3-(tert-butyldimethylsilanyloxy)-5-hydroxy-2,4-dimethylhexananoic acid methoxymethyl amide
  参考文献：
  名称：

  Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 2:  Synthesis of Fragments C_1-6 and C_9-14

  摘要：

  Kilogram-scale syntheses of fragments C1-6 (6) and C9-14 (4) of (+)-discodermolide from common precursor 3 are described. Improved procedures for each step of both fragments were developed by minimizing or eliminating the formation of byproducts that were isolated and characterized in Smith's synthesis.

  DOI：

  10.1021/op0341317

文献信息

• PROCESS FOR PREPARING DISCODERMOLIDE AND ANALOGUES THEREOF
  申请人：——

  公开号：US20020198389A1

  公开（公告）日：2002-12-26

  A more practical synthesis for preparing discodermolide and structurally related analogues, novel compounds useful in the process and novel compounds prepared by the process.

  一种更实用的合成方法，用于制备discodermolide及其结构类似物，该过程中有用的新化合物和通过该过程制备的新化合物。
• Process for preparing discodermolide and analogues thereof
  申请人：Novartis AG

  公开号：US06506910B1

  公开（公告）日：2003-01-14

  A more practical synthesis for preparing discodermolide and structurally related analogues, novel compounds useful in the process and novel compounds prepared by the process.

  一种更实用的合成方法，用于制备discodermolide及其结构相关的类似物，以及在该过程中有用的新化合物和通过该过程制备的新化合物。
• Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 2:  Synthesis of Fragments C₁_-₆ and C_9-14
  作者：Stuart J. Mickel、Gottfried H. Sedelmeier、Daniel Niederer、Friedrich Schuerch、Dominique Grimler、Guido Koch、Robert Daeffler、Adnan Osmani、Alfred Hirni、Karl Schaer、Remo Gamboni、Andrew Bach、Apurva Chaudhary、Stephen Chen、Weichun Chen、Bin Hu、Christopher T. Jagoe、Hong-Yong Kim、Frederick R. Kinder、Yugang Liu、Yansong Lu、Joseph McKenna、Mahavir Prashad、Timothy M. Ramsey、Oljan Repič、Larry Rogers、Wen-Chung Shieh、Run-Ming Wang、Liladhar Waykole

  DOI：10.1021/op0341317

  日期：2004.1.1

  Kilogram-scale syntheses of fragments C1-6 (6) and C9-14 (4) of (+)-discodermolide from common precursor 3 are described. Improved procedures for each step of both fragments were developed by minimizing or eliminating the formation of byproducts that were isolated and characterized in Smith's synthesis.
• A Formal Synthesis of (+)-Discodermolide
  作者：Olivier Loiseleur、Guido Koch、Jacques Cercus、Friedrich Schürch

  DOI：10.1021/op049807s

  日期：2005.5.1

  Herein, we report the formal synthesis of (+)-discodermolide (1), a promising anticancer agent of sponge origin, in 24 linear steps, with 35 steps in total. The route proceeds from lactone 2, a building block containing the common 1,2-anti-2,3-syn stereotriad found in each of the three subunits, methyl ketone 4 (C-1-C-6), vinyl iodide 7 (C-9--C-14), and iodide 8 (C-15-C-24) utilized for the construction of L The key fragment union was achieved by a Suzuki cross-coupling between 7 and 8.