(2R)-1-(3,4-dimethoxyphenyl)-2-[4-[(2S,3R,4R,5S)-5-[4-[(2R)-1-(3,4-dimethoxyphenyl)-1-oxopropan-2-yl]oxy-3-methoxyphenyl]-3,4-dimethyloxolan-2-yl]-2-methoxyphenoxy]propan-1-one | 915158-69-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (2R)-1-(3,4-dimethoxyphenyl)-2-[4-[(2S,3R,4R,5S)-5-[4-[(2R)-1-(3,4-dimethoxyphenyl)-1-oxopropan-2-yl]oxy-3-methoxyphenyl]-3,4-dimethyloxolan-2-yl]-2-methoxyphenoxy]propan-1-one
• CAS: 915158-69-9
• 化学式: C₄₂H₄₈O₁₁
• 分子量: 728.837
• InChiKey: XQKWZFOJRRNGGD-BRBRLKMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R)-1-(3,4-dimethoxyphenyl)-2-[4-[(2S,3R,4R,5S)-5-[4-[(2R)-1-(3,4-dimethoxyphenyl)-1-oxopropan-2-yl]oxy-3-methoxyphenyl]-3,4-dimethyloxolan-2-yl]-2-methoxyphenoxy]propan-1-one 在 Amberlite IRA-400-supported borohydride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以76%的产率得到manassantin A
  参考文献：
  名称：

  Total Synthesis and Stereochemical Confirmation of Manassantin A, B, and B₁

  摘要：

  Stereocontrolled total syntheses of manassantins A, B, and B-1 and saucerneol are described for the first time based on a novel cycloetherification of end-differentiated benzylic alcohols as a common intermediate.

  DOI：

  10.1021/ol0621710
• 作为产物：
  描述：

  (1R,2R,3R,4S)-4-[4-(4-benzyloxy-3-methoxyphenyl)-1-hydroxy-4-methoxymethoxy-2,3-dimethylbutyl]-2-methoxyphenol 在 palladium dihydroxide 氢气 、 二甲基氯化铝 、 甲基磺酰氯 、 2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.58h， 生成 (2R)-1-(3,4-dimethoxyphenyl)-2-[4-[(2S,3R,4R,5S)-5-[4-[(2R)-1-(3,4-dimethoxyphenyl)-1-oxopropan-2-yl]oxy-3-methoxyphenyl]-3,4-dimethyloxolan-2-yl]-2-methoxyphenoxy]propan-1-one
  参考文献：
  名称：

  Total Synthesis and Stereochemical Confirmation of Manassantin A, B, and B₁

  摘要：

  Stereocontrolled total syntheses of manassantins A, B, and B-1 and saucerneol are described for the first time based on a novel cycloetherification of end-differentiated benzylic alcohols as a common intermediate.

  DOI：

  10.1021/ol0621710

文献信息

• [EN] MANASSANTIN COMPOUNDS AND METHODS OF MAKING AND USING SAME<br/>[FR] COMPOSÉS DE MANASSANTIN ET LEURS PROCÉDÉS DE PRODUCTION ET D'UTILISATION
  申请人：UNIV DUKE

  公开号：WO2010059858A1

  公开（公告）日：2010-05-27

  Provided are manassantin compounds and methods of using the compounds. Provided are methods of treating a disease, the method comprising administering a compound according to Formula I. Further provided are pharmaceutical compositions comprising compounds according to Formula I. Also provided are methods of inhibiting HIF-1 in a cell, the methods comprising administering to the cell a compound according to Formula I.

  提供了manassantin化合物和使用该化合物的方法。提供了治疗疾病的方法，该方法包括给予符合公式I的化合物。另外提供了包含符合公式I的化合物的药物组合物。还提供了在细胞中抑制HIF-1的方法，该方法包括给予细胞符合公式I的化合物。
• Nucleophilic Addition of Organozinc Reagents to 2-Sulfonyl Cyclic Ethers: Stereoselective Synthesis of Manassantins A and B
  作者：Hyoungsu Kim、Amanda C. Kasper、Eui Jung Moon、Yongho Park、Ceshea M. Wooten、Mark W. Dewhirst、Jiyong Hong

  DOI：10.1021/ol8024617

  日期：2009.1.1

  A convergent route to the synthesis of manassantins A and B, potent Inhibitors of HIF-1, is described. Central to the synthesis is a stereoselective addition of an organozinc reagent to a 2-benzenesulfonyl cyclic ether to achieve the 2,3-cis-3,4-trans-4,5-cis-tetrahydrofuran of the natural products. Preliminary structure-activity relationships suggested that the (R)-configuration at C-7 and C-7''' is not critical for HIF-1 inhibition. In addition, the hydroxyl group at C-7 and C-7''' can be replaced with a carbonyl group without loss of activity.
• US8946289B2
  申请人：——

  公开号：US8946289B2

  公开（公告）日：2015-02-03
• Total Synthesis and Stereochemical Confirmation of Manassantin A, B, and B₁
  作者：Stephen Hanessian、Gone Jayapal Reddy、Navjot Chahal

  DOI：10.1021/ol0621710

  日期：2006.11.1

  Stereocontrolled total syntheses of manassantins A, B, and B-1 and saucerneol are described for the first time based on a novel cycloetherification of end-differentiated benzylic alcohols as a common intermediate.