4-[(2S,3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol | 198877-17-7

• 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: 4-[(2S,3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
• CAS: 198877-17-7
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: GMXMKSFJQLFOSO-ZDEMKHDWSA-N

物化性质

• 沸点：
  509.7±50.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(2S,3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol 在 二甲基氯化铝 、 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 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 (R)-N-Methoxy-2-[2-methoxy-4-((2S,3R,4R,5S)-5-{3-methoxy-4-[(R)-1-(methoxy-methyl-carbamoyl)-ethoxy]-phenyl}-3,4-dimethyl-tetrahydro-furan-2-yl)-phenoxy]-N-methyl-propionamide
  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 、 lithium hydroxide 、 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 4-[(2S,3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
  参考文献：
  名称：

  2,5-二芳基-3,4-二甲基四氢呋喃木脂素的全合成和立体化学确认：(+)-Fragransin A2、(+)-Galbelgin、(+)-Talaumidin、(-)-Saucernetin 和 (-)-Verrucosin

  摘要：

  从 OMOM 醚分子内攻击到甲磺酸苄酯的四取代四氢呋喃的新闭环通过醌类中间体或通过直接 SN 2 置换进行。使用这种通用方法描述了非对映异构生物活性天然木脂素的合成。

  DOI：

  10.1055/s-2007-968019

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.
• Synthesis of All Stereoisomers of 3,3′-Dimethoxy-7,7′-epoxylignane-4,4′-diol and Their Plant Growth Inhibitory Activity
  作者：Hisashi Nishiwaki、Kumiko Nakayama、Yoshihiro Shuto、Satoshi Yamauchi

  DOI：10.1021/jf4046396

  日期：2014.1.22

  All stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol were synthesized to examine the effect of stereochemistry on their plant growth inhibitory activity using lettuce and Italian ryegrass. The effect of structural modifications such as dehydroxylation, methoxylation and hydroxylation at the 9- and 9'-positions of the lignans on the activity was also studied. Most of the epoxylignanes showed higher plant growth inhibitory potency against ryegrass than against lettuce, and the inhibitory activity varied depending on the configurations of each position of the tetrahydrofuran ring (7-, 7'-, 8-, and 8'-positions of the epoxylignanes). Among the 9,9'-position-modified derivatives, the dehydroxy derivatives showed the highest potency. These results suggested that the plant growth inhibitory activity should be influenced by the structure of the epoxylignanes.
• 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.
• Total Synthesis and Stereochemical Confirmation of 2,5-Diaryl-3,4-dimethyltetrahydrofuran Lignans: (+)-Fragransin A₂, (+)-Galbelgin, (+)-Talaumidin, (-)-Saucernetin and (-)-Verrucosin
  作者：Stephen Hanessian、Gone Reddy

  DOI：10.1055/s-2007-968019

  日期：2007.2

  A new ring closure to tetrasubstituted tetrahydrofurans from the intramolecular attack of an OMOM ether onto a benzylic mesylate proceeds through a quinonoid intermediate or by direct S N 2 displacement. The synthesis of diastereomeric biologically active natural lignans is described utilizing this general methodology.

  从 OMOM 醚分子内攻击到甲磺酸苄酯的四取代四氢呋喃的新闭环通过醌类中间体或通过直接 SN 2 置换进行。使用这种通用方法描述了非对映异构生物活性天然木脂素的合成。