(2R,4R,6S,8S,10S)-2,4,6,8-tetrahydroxy-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)pentacosan-10-yl acetate | 1307232-01-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,4R,6S,8S,10S)-2,4,6,8-tetrahydroxy-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)pentacosan-10-yl acetate
• 英文别名: cryptocaryol B；(2R,4R,6S,8S,10S)-2,4,6,8-tetrahydroxy-1-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]pentacosan-10-yl acetate；[(2R,4R,6S,8S,10S)-2,4,6,8-tetrahydroxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]pentacosan-10-yl] acetate
• CAS: 1307232-01-4
• 化学式: C₃₂H₅₈O₈
• 分子量: 570.808
• InChiKey: JUDSGWKIMNPKNH-XSFYONRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  40
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,4R,6S,8S,10S)-2,4,6,8-tetrahydroxy-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)pentacosan-10-yl acetate 在 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以66%的产率得到(2R,4R,6S,8S,10S)-2,4,6,8-tetrahydroxy-1-((R)-6-oxotetrahydro-2H-pyran-2-yl)pentacosan-10-yl acetate
  参考文献：
  名称：

  Cryptocaryols A and B: Total Syntheses, Stereochemical Revision, Structure Elucidation, and Structure–Activity Relationship

  摘要：

  The first total syntheses and structural elucidation of cryptocaryol A and ayptocaryol B were achieved in 23 and 25 linear steps, respectively. The synthesis relied on the use Of a key pseudo-C, symmetric pentaol intermediate, which in a stereochemically divergent manner was converted into either enantiomer as well as diastereomers. This synthetic effort enabled the first structure-activity relationships of this class of PDCD4 stabilizing natural products.

  DOI：

  10.1021/ja404401f
• 作为产物：
  描述：

  ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate 在 咪唑 、 Grubbs catalyst first generation 、 4-二甲氨基吡啶 、 正丁基锂 、 甲酸 、 氯化(均三甲苯)[(R,R)-N-(对甲苯磺酰基)-1,2-二苯乙烯基二胺]钌(II) 、 2-硝基苯磺酰肼 、 四丁基氟化铵 、 水 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.63h， 生成 (2R,4R,6S,8S,10S)-2,4,6,8-tetrahydroxy-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)pentacosan-10-yl acetate
  参考文献：
  名称：

  隐烯醇A和B的多烯策略的不对称迭代水合

  摘要：

  摘要 两种迭代不对称水合的发展接近所有的合成顺式-和顺式/反/顺式-1,3,5,7四醇基序进行说明。这些伪对称产物是1，3-己醇产物的合成前体。证明了该路线对所有syn -1,3,5,7-四醇非对映异构体的实用性，并证明其可用于合成隐甲酚A和B，以及立体异构体。 两种迭代不对称水合的发展接近所有的合成顺式-和顺式/反/顺式-1,3,5,7四醇基序进行说明。这些伪对称产物是1，3-己醇产物的合成前体。证明了该路线对所有syn -1,3,5,7-四醇非对映异构体的实用性，并证明其可用于合成隐甲酚A和B，以及立体异构体。

  DOI：

  10.1055/s-0035-1561607

文献信息

• Cryptocaryol Structure–Activity Relationship Study of Cancer Cell Cytotoxicity and Ability to Stabilize PDCD4
  作者：Michael F. Cuccarese、Yanping Wang、Penny J. Beuning、George A. O’Doherty

  DOI：10.1021/ml4005039

  日期：2014.5.8

  The synthetic cryptocaryols A and B and a series of their analogues have been evaluated for their cytotoxicity and their ability to stabilize the tumor suppressor PDCD4. Cytotoxicities in the 3 to 30 mu M range were found. Both the cytotoxicity and PDCD4 stabilizing ability were tolerant of large stereochemical changes to the molecule. Co-dosing studies with cryptocaryols A and B and several known cancer drugs showed no measuable enhancement in cancer drug cytotoxicity.
• Asymmetric Iterative Hydration of Polyene Strategy to Cryptocaryols A and B
  作者：George O’Doherty、Thomas Hunter、Yanping Wang、Jiamin Zheng

  DOI：10.1055/s-0035-1561607

  日期：——

  development of two iterative asymmetric hydration approaches to the synthesis of all syn- and syn/anti/syn-1,3,5,7-tetraol motifs is described. These pseudo-symmetric products are synthetic precursors for 1,3-hexol products. The utility of the route to the all syn-1,3,5,7-tetraol diastereoisomer was demonstrated with its use in the synthesis of cryptocaryols A and B, as well as, stereoisomers. The development

  摘要 两种迭代不对称水合的发展接近所有的合成顺式-和顺式/反/顺式-1,3,5,7四醇基序进行说明。这些伪对称产物是1，3-己醇产物的合成前体。证明了该路线对所有syn -1,3,5,7-四醇非对映异构体的实用性，并证明其可用于合成隐甲酚A和B，以及立体异构体。 两种迭代不对称水合的发展接近所有的合成顺式-和顺式/反/顺式-1,3,5,7四醇基序进行说明。这些伪对称产物是1，3-己醇产物的合成前体。证明了该路线对所有syn -1,3,5,7-四醇非对映异构体的实用性，并证明其可用于合成隐甲酚A和B，以及立体异构体。
• Cryptocaryols A and B: Total Syntheses, Stereochemical Revision, Structure Elucidation, and Structure–Activity Relationship
  作者：Yanping Wang、George A. O’Doherty

  DOI：10.1021/ja404401f

  日期：2013.6.26

  The first total syntheses and structural elucidation of cryptocaryol A and ayptocaryol B were achieved in 23 and 25 linear steps, respectively. The synthesis relied on the use Of a key pseudo-C, symmetric pentaol intermediate, which in a stereochemically divergent manner was converted into either enantiomer as well as diastereomers. This synthetic effort enabled the first structure-activity relationships of this class of PDCD4 stabilizing natural products.