(1R,2R)-1-(3',5'-dibenzyloxyphenyl)-3-(2''-methoxymethyloxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol | 863237-52-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1R,2R)-1-(3',5'-dibenzyloxyphenyl)-3-(2''-methoxymethyloxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol
• 英文别名: (1R,2R)-3-(2,4-bis(benzyloxy)-6-(methoxymethoxy)-phenyl)-1-(3,5-bis(benzyloxy)phenyl)propane-1,2-diol；(1R,2R)-1-[3,5-bis(phenylmethoxy)phenyl]-3-[2-(methoxymethoxy)-4,6-bis(phenylmethoxy)phenyl]propane-1,2-diol
• CAS: 863237-52-9
• 化学式: C₄₅H₄₄O₈
• 分子量: 712.84
• InChiKey: ZCZIIWXZEUYDIC-RHKHYPKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.62
• 重原子数：
  53.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  95.84
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-(3',5'-dibenzyloxyphenyl)-3-(2''-methoxymethyloxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 5.0h， 生成 (1R,2R)-1-(3',5'-dibenzyloxyphenyl)-3-(2''-hydroxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol
  参考文献：
  名称：

  Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus

  摘要：

  Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.086
• 作为产物：
  描述：

  4,6-dibenzyloxy-2-methoxymethyloxybenzaldehyde 在 氢氧化钾 、 sodium tetrahydroborate 、 甲基磺酰胺 、 AD-mix-β 、 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 136.0h， 生成 (1R,2R)-1-(3',5'-dibenzyloxyphenyl)-3-(2''-methoxymethyloxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol
  参考文献：
  名称：

  Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus

  摘要：

  Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.086

文献信息

• Enantio Selective Synthesis of New Phenylpropanoid: Isolated from Walsura trifoliata
  作者：L.V. Ramana、M. Suri Appa Rao、K.M. Ch. Apparao、B. Nageswara Rao

  DOI：10.14233/ajchem.2019.22064

  日期：2019.8.10

  A new phenylpropanoid containing flavon-3-ol has been isolated from the leaves of traditional medicinal plant, Walsura trifoliata. The structure of the compound was established on the basis of spectroscopic evidence [2D NMR, HREIMS] and by its alternative synthesis. The synthesis of this natural product was achieved from inexpensive and readily available starting materials of phloroglucinol dihydrate. Key reaction sequence includes Grubbs-II RCM reaction, Wittig reaction and sharpless dihydroxylation using AD-mix α.

  从传统药用植物Walsura trifoliata的叶中分离出一种含有黄酮-3-醇的新苯丙烷类化合物。该化合物的结构是基于光谱证据[2D NMR，HREIMS]和其替代合成确定的。这种天然产物的合成是从廉价且易得的起始材料邻苯三酚二水合物中实现的。关键反应序列包括Grubbs-II RCM反应，Wittig反应和利用AD-mix α的Sharpless二羟基化反应。