(1S,2S)-1,2-dihydroxy-1-[2',3'-di(tert-butyldimethylsilyloxy)-4'-methoxyphenyl]-2-(3'',4'',5''-trimethoxyphenyl)ethane | 290295-01-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2S)-1,2-dihydroxy-1-[2',3'-di(tert-butyldimethylsilyloxy)-4'-methoxyphenyl]-2-(3'',4'',5''-trimethoxyphenyl)ethane
• 英文别名: (1S,2S)-1-[2',3'-di[(tert-butyldimethylsilyl)oxy]-4'-methoxyphenyl]-2-(3,4,5-trimethoxyphenyl)ethane-1,2-diol；(1S,2S)-1-[2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyphenyl]-2-(3,4,5-trimethoxyphenyl)ethane-1,2-diol
• CAS: 290295-01-1
• 化学式: C₃₀H₅₀O₈Si₂
• 分子量: 594.893
• InChiKey: WPVNAGXTXNTVBQ-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1,2-dihydroxy-1-[2',3'-di(tert-butyldimethylsilyloxy)-4'-methoxyphenyl]-2-(3'',4'',5''-trimethoxyphenyl)ethane 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以68%的产率得到(+/-)-2-(2',3'-di[(tert-butyldimethylsilyl)oxy]-4'-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acetaldehyde
  参考文献：
  名称：

  A Pinacol Rearrangement/Oxidation Synthetic Route to Hydroxyphenstatin¹

  摘要：

  In an attempt to develop biologically active compounds from the inactive trans isomer (3a) of stilbene la, after asymmetric dihydroxylation to optically pure (R,R)-diol 8 the unexpected racemic diphenylacetaldehyde (9) was generated via a Pinacol rearrangement. Several derivatives of diphenylacetaldehyde 9 were synthesized (11-15) and reported. Further reaction of aldehyde 9 during desilylation through autoxidative decarbonylation afforded benzophenone 2b, designated hydroxyphenstatin, a potent antitumor and antimitotic agent. Hydroxyphenstatin showed potent inhibition of the tubulin assembly (IC50 0.82 muM) and exhibited an ED50 of 2.5 mug/mL against the P388 lymphocytic leukemia cell line.

  DOI：

  10.1021/jo000705j
• 作为产物：
  描述：

  (E)-1-[3',4',5'-trimethoxyphenyl]-2-[(2'',3''-di[(tert-butyldimethylsilyl)oxy]-4''-methoxy)phenyl]ethene 在 AD-mix-α 、 水 作用下， 以 叔丁醇 为溶剂， 以75%的产率得到(1S,2S)-1,2-dihydroxy-1-[2',3'-di(tert-butyldimethylsilyloxy)-4'-methoxyphenyl]-2-(3'',4'',5''-trimethoxyphenyl)ethane
  参考文献：
  名称：

  抗肿瘤药440.康布雷他汀A-1 SAR探针（1S，2S）-和（1R，2R）-1，2-二羟基-1-（2'，3'-二羟基-4'-甲氧基苯基）的不对称合成和评估）-2-（3''，4''，5''-三甲氧基苯基）-乙烷。

  摘要：

  从非洲灌木柳Combrtum牛aff中分离得到的天然康维他汀A-1（1a）的合成（E）-异构体（3b）是手性羟基化（Sharpless）反应的重点，是结构-活性关系研究的一部分。针对一系列癌细胞系，微生物和微管蛋白评估了生成的（R，R）-和（S，S，）-二醇（6和7）和合成中间体。与前体（E）-二苯乙烯3b相比，手性二醇6和7对P-388鼠淋巴细胞性白血病细胞系的ED（50）值分别为3.9和2.9 microg / mL，活性增强。相反，（E）-二苯乙烯3b表现出比手性二醇更强的抗生素活性（6和7）。（R，R）-6和（S，S）-7两个二醇

  DOI：

  10.1021/np0000623

文献信息

• A Pinacol Rearrangement/Oxidation Synthetic Route to Hydroxyphenstatin¹
  作者：George R. Pettit、John W. Lippert、Delbert L. Herald

  DOI：10.1021/jo000705j

  日期：2000.11.1

  In an attempt to develop biologically active compounds from the inactive trans isomer (3a) of stilbene la, after asymmetric dihydroxylation to optically pure (R,R)-diol 8 the unexpected racemic diphenylacetaldehyde (9) was generated via a Pinacol rearrangement. Several derivatives of diphenylacetaldehyde 9 were synthesized (11-15) and reported. Further reaction of aldehyde 9 during desilylation through autoxidative decarbonylation afforded benzophenone 2b, designated hydroxyphenstatin, a potent antitumor and antimitotic agent. Hydroxyphenstatin showed potent inhibition of the tubulin assembly (IC50 0.82 muM) and exhibited an ED50 of 2.5 mug/mL against the P388 lymphocytic leukemia cell line.
• Antineoplastic Agents 440. Asymmetric Synthesis and Evaluation of the Combretastatin A-1 SAR Probes (1<i>S</i>,2<i>S</i>)- and (1<i>R</i>,2<i>R</i>)-1,2-Dihydroxy- 1-(2‘,3‘-dihydroxy-4‘-methoxyphenyl)-2-(3‘ ‘,4‘ ‘,5‘ ‘-trimethoxyphenyl)-ethane
  作者：George R. Pettit、John W. Lippert、Delbert L. Herald、Ernest Hamel、Robin K. Pettit

  DOI：10.1021/np0000623

  日期：2000.7.1

  combretastatin A-1 (1a) isolated from the African bushwillow Combretum caffrum was the focus of chiral hydroxylation (Sharpless) reactions as part of a structure-activity relationship study. The resulting (R,R)- and (S,S, )-diols (6 and 7) and synthetic intermediates were evaluated against a series of cancer cell lines, microorganisms, and tubulin. Chiral diols 6 and 7 showed increased activity against the P-388

  从非洲灌木柳Combrtum牛aff中分离得到的天然康维他汀A-1（1a）的合成（E）-异构体（3b）是手性羟基化（Sharpless）反应的重点，是结构-活性关系研究的一部分。针对一系列癌细胞系，微生物和微管蛋白评估了生成的（R，R）-和（S，S，）-二醇（6和7）和合成中间体。与前体（E）-二苯乙烯3b相比，手性二醇6和7对P-388鼠淋巴细胞性白血病细胞系的ED（50）值分别为3.9和2.9 microg / mL，活性增强。相反，（E）-二苯乙烯3b表现出比手性二醇更强的抗生素活性（6和7）。（R，R）-6和（S，S）-7两个二醇