3-benzyloxy-4-hydroxy-trans-cinnamic acid methyl ester | 868671-93-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-benzyloxy-4-hydroxy-trans-cinnamic acid methyl ester
• CAS: 868671-93-6
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: XUSHXYNVLXMESF-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-4-hydroxy-trans-cinnamic acid methyl ester 在 4 A molecular sieve 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 (E)-3-[3-Benzyloxy-4-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester
  参考文献：
  名称：

  Synthesis of the Saccharomicin Fucose−Aglycon Conjugate and Determination of Absolute Configuration

  摘要：

  Schmidt glycosylation of the appropriately protected 3,4-dihydroxycinnamate methyl ester with 2,3,4-triacetoxyfucopyranosyltrichloroacetimidate gives aryl glycoside in high yield and diastereoselectivity. 2-Sulfation of fucose, installation of taurine, and global deprotection of the remaining protecting groups affords the fucose-aglycon conjugate of saccharomicin. This synthesis which arises from L-fucose also establishes the absolute configuration of the reducing terminus of the saccharomicin oligosaccharide.

  DOI：

  10.1021/ol051971s
• 作为产物：
  描述：

  TRANS-咖啡酸 在 硫酸 、 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 13.0h， 生成 3-benzyloxy-4-hydroxy-trans-cinnamic acid methyl ester
  参考文献：
  名称：

  New derivatives of silybin and 2,3-dehydrosilybin and their cytotoxic and P-glycoprotein modulatory activity

  摘要：

  Large series of O-alkyl derivatives (methyl and benzyl) of silybin and 2,3-dehydrosilybin was prepared. Selective alkylation of the silybin molecule was systematically investigated. For the first time we present here, for example, preparation of 19-nor-2,3-dehydrosilybin. All prepared silybin/2.3-dehydrosilybin derivatives were tested for cytotoxicity on a panel of drugs sensitive against multidrug resistant cell lines and the ability to inhibit P-glycoprotein mediated efflux activity. We have identified effective and relatively non-cytotoxic inhibitors of P-gp derived from 2,3-dehydrosilybin. Some of them were more effective inhibitors at concentrations lower than a standard P-gp efflux inhibitor cyclosporin A. Another group of 2,3-dehydrosilybin derivatives also had better inhibitory effects on P-gp efflux but a cytotoxicity comparable with that of parent 2,3-dehydrosilybin. Structural requirements for improving inhibitory activity and reducing toxicity of 2,3-dehydrosilybin were established. Effect of E-ring substitution as well as an influence of the substituent size at the C-7-OH position of A-ring on P-gp-inhibitory activity was evaluated for the first time in this study. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.035