(2R,3S,4S)-3-(methoxymethoxy)-5-[(4-methoxyphenyl)methoxy]-2,4-dimethylpentanal | 633293-87-5

• 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: (2R,3S,4S)-3-(methoxymethoxy)-5-[(4-methoxyphenyl)methoxy]-2,4-dimethylpentanal
• CAS: 633293-87-5
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: KYOKMONJBARNDU-GRDNDAEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-3-(methoxymethoxy)-5-[(4-methoxyphenyl)methoxy]-2,4-dimethylpentanal 在 咪唑 、 水 、 叔丁基锂 、 二异丁基氢化铝 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc(II) chloride 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， 反应 28.0h， 生成 (2S,3S,4R,5R,6S,10S,11R,12S)-5,13-bis[[tert-butyl(dimethyl)silyl]oxy]-11-(methoxymethoxy)-3-[(4-methoxyphenyl)methoxy]-2,4,6,8,10,12-hexamethyltridec-8-en-1-ol
  参考文献：
  名称：

  A Practical Improvement, Enhancing the Large-Scale Synthesis of (+)-Discodermolide:  A Third-Generation Approach

  摘要：

  A significant improvement to the Penn one-gram synthesis of (+)-discodermolide (1) has been achieved. Specifically, reduction of the steric bulk of the C(11) hydroxyl protecting group permits formation of the requisite AB Wittig salt at the expense of the undesired intramolecular cyclization upon treatment with PPh3 at ambient pressure.

  DOI：

  10.1021/ol035697i
• 作为产物：
  描述：

  (2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide 在 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.17h， 生成 (2R,3S,4S)-3-(methoxymethoxy)-5-[(4-methoxyphenyl)methoxy]-2,4-dimethylpentanal
  参考文献：
  名称：

  A Practical Improvement, Enhancing the Large-Scale Synthesis of (+)-Discodermolide:  A Third-Generation Approach

  摘要：

  A significant improvement to the Penn one-gram synthesis of (+)-discodermolide (1) has been achieved. Specifically, reduction of the steric bulk of the C(11) hydroxyl protecting group permits formation of the requisite AB Wittig salt at the expense of the undesired intramolecular cyclization upon treatment with PPh3 at ambient pressure.

  DOI：

  10.1021/ol035697i

文献信息

• A Practical Approach to Synthesize the C(9) -C(24) Fragment of (+)-Discodermolide
  作者：Zengsheng Yin、Xuyi Yue、Xiangjun Deng、Fengling Qing

  DOI：10.1002/cjoc.201090240

  日期：——

  A practical and stereoselective synthesis of the C(9)–C(24) subunit of (+)‐discodermolide has been achieved. The strategy featured the construction of the key intermediate Z‐trisubstituted vinyl iodide 12 from the dibromo‐olefin 6 via an efficient modified Tanino‐Miyashita's approach. The union of the two fragments was carried out through a Suzuki cross‐coupling reaction.

  （+）-discodermolide的C（9）–C（24）亚基的实用且立体选择性合成已实现。该策略的特色是通过有效的改进的Tanino-Miyashita方法，由二溴烯烃6构建关键的中间体Z-三取代乙烯基碘12。这两个片段的结合是通过铃木交叉偶联反应进行的。
• [EN] SYNTHETIC TECHNIQUES AND INTERMEDIATES FOR POLYHYDROXY DIENYL LACTONES AND MIMICS THEREOF<br/>[FR] TECHNIQUES DE SYNTHESE ET INTERMEDIAIRES POUR LACTONES DE DIENYLE POLYHYDROXYLE ET LEURS ANALOGUES
  申请人：UNIV PENNSYLVANIA

  公开号：WO2004101508A3

  公开（公告）日：2005-03-03
• Scalable, Catalytic Asymmetric Synthesis of Syn, Anti Stereotriad Building Blocks for Polypropionate Antibiotics
  作者：Kathlyn A. Parker、Huanyan Cao

  DOI：10.1021/ol0612612

  日期：2006.8.1

  Asymmetric catalysis and chirality transfer by the 2,3-Wittig rearrangement were combined to provide a syn, anti stereotriad-containing olefinic alcohol in five steps from inexpensive starting materials. Development of this compound, a versatile intermediate for polypropionate synthesis, gave known building blocks for discodermolide.
• US7342124B2
  申请人：——

  公开号：US7342124B2

  公开（公告）日：2008-03-11
• A Practical Improvement, Enhancing the Large-Scale Synthesis of (+)-Discodermolide:  A Third-Generation Approach
  作者：Amos B. Smith、B. Scott Freeze、Ignacio Brouard、Tomoyasu Hirose

  DOI：10.1021/ol035697i

  日期：2003.11.1

  A significant improvement to the Penn one-gram synthesis of (+)-discodermolide (1) has been achieved. Specifically, reduction of the steric bulk of the C(11) hydroxyl protecting group permits formation of the requisite AB Wittig salt at the expense of the undesired intramolecular cyclization upon treatment with PPh3 at ambient pressure.