[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxybutoxy]oxan-2-yl]methyl benzoate | 1456548-38-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷
• 英文名称: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxybutoxy]oxan-2-yl]methyl benzoate
• CAS: 1456548-38-1
• 化学式: C₈₈H₇₈O₂₄
• 分子量: 1519.57
• InChiKey: AUDWDNIOHIJRFO-IJTOEPSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  112
• 可旋转键数：
  39
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  306
• 氢给体数：
  2
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxybutoxy]oxan-2-yl]methyl benzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 60.0h， 以81%的产率得到2,3-双(3-甲氧基-4-羟基苄基)丁烷-1,4-二醇 1,4-二葡萄糖甙
  参考文献：
  名称：

  [EN] PREPARATION OF (S,S)-SECOISOLARICIRESINOL DIGLUCOSIDE AND (R,R)-SECOISOLARICIRESINOL DIGLUCOSIDE
  [FR] PRÉPARATION DE (S,S)-SÉCOISOLARICIRÉSINOL DIGLUCOSIDE ET DE (R,R)-SÉCOISOLARICIRÉSINOL DIGLUCOSIDE

  摘要：

  该发明涉及制备（S，S）-丝氨酸木脂糖苷和（R，R）-丝氨酸木脂糖苷的过程以及包含它们的组合物。

  公开号：

  WO2014200964A1
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[2,3-bis[(3-methoxy-4-phenylmethoxyphenyl)methyl]-4-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxybutoxy]oxan-2-yl]methyl benzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2S,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxybutoxy]oxan-2-yl]methyl benzoate 、 [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxybutoxy]oxan-2-yl]methyl benzoate
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF (S,S)-SECOISOLARICIRESINOL DIGLUCOSIDE AND (R,R)-SECOISOLARICIRESINOL DIGLUCOSIDE
  [FR] PRÉPARATION DE (S,S)-SÉCOISOLARICIRÉSINOL DIGLUCOSIDE ET DE (R,R)-SÉCOISOLARICIRÉSINOL DIGLUCOSIDE

  摘要：

  提供了一种(S,S)-丝光木素二葡萄糖苷和(R,R)-丝光木素二葡萄糖苷的合成过程。

  公开号：

  WO2018231691A1

文献信息

• Synthesis and antioxidant evaluation of (S,S)- and (R,R)-secoisolariciresinol diglucosides (SDGs)
  作者：Om P. Mishra、Nicholas Simmons、Sonia Tyagi、Ralph Pietrofesa、Vladimir V. Shuvaev、Roman A. Valiulin、Philipp Heretsch、K.C. Nicolaou、Melpo Christofidou-Solomidou

  DOI：10.1016/j.bmcl.2013.07.062

  日期：2013.10

  Secoisolariciresinol diglucosides (SDGs) (S,S)-SDG-1 (major isomer in flaxseed) and (R,R)-SDG-2 (minor isomer in flaxseed) were synthesized from vanillin via secoisolariciresinol (6) and glucosyl donor 7 through a concise route that involved chromatographic separation of diastereomeric diglucoside derivatives (S,S)-8 and (R,R)-9. Synthetic (S,S)-SDG-1 and (R, R)-SDG-2 exhibited potent antioxidant properties (EC50 = 292.17 +/- 27.71 mu M and 331.94 +/- 21.21 mu M, respectively), which compared well with that of natural (S,S)-SDG-1 (EC50 = 275.24 +/- 13.15 mu M). These values are significantly lower than those of ascorbic acid (EC50 = 1129.32 +/- 88.79 mu M) and a-tocopherol (EC50 = 944.62 +/- 148.00 mu M). Compounds (S,S)SDG-1 and (R, R)-SDG-2 also demonstrated powerful scavenging activities against hydroxyl [natural (S,S)-SDG-1: 3.68 +/- 0.27; synthetic (S,S)-SDG-1: 2.09 +/- 0.16; synthetic (R,R)-SDG-2: 1.96 +/- 0.27], peroxyl [natural (S,S)-SDG-1: 2.55 +/- 0.11; synthetic (S,S)-SDG-1: 2.20 +/- 0.10; synthetic (R,R)-SDG-2: 3.03 +/- 0.04] and DPPH [natural (S, S)-SDG-1: EC50 = 83.94 +/- 2.80 mu M; synthetic (S, S)-SDG-1: EC50 = 157.54 +/- 21.30 lM; synthetic (R, R)-SDG-2: EC50 = 123.63 +/- 8.67 mu M] radicals. These results confirm previous studies with naturally occurring (S,S)-SDG-1 and establish both (S, S)-SDG-1 and (R,R)-SDG-2 as potent antioxidants and free radical scavengers for potential in vivo use. (C) 2013 Elsevier Ltd. All rights reserved.