Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-((R)-2,3-bis-benzyloxy-propoxy)-6-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester | 832719-96-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-((R)-2,3-bis-benzyloxy-propoxy)-6-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester
• CAS: 832719-96-7
• 化学式: C₄₃H₅₄O₂₀
• 分子量: 890.89
• InChiKey: SWGZKFYTZLJXBM-OEMNOAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  63.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  239.48
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-((R)-2,3-bis-benzyloxy-propoxy)-6-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 甲醇 、 氢气 、 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 3.17h， 生成 (2R)-1-O-[α-D-galactopyranosyl-(1''->6')-O-β-D-galactopyranosyl] glycerol
  参考文献：
  名称：

  Synthesis of digalactosyl diacylglycerols and their structure–inhibitory activity on human lanosterol synthase

  摘要：

  Digalactosyl and monogalactocyl diacylglycerols (DGDG and MGDG), which were identified as anti-hyperlipemia active components in Colocasia esculenta (Taro), were synthesized. The inhibitory activity of DGDG, MGDG and related compounds on human lanosterol synthase was evaluated as anti-hyperlipemic activity. DGDG with two myristoyl groups at both sn-1 and sn-2 positions and with an oleoyl group at the sn-1 position showed the most potent activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.013
• 作为产物：
  描述：

  Acetic acid (3R,4S,5S,6R)-2,3,5-triacetoxy-6-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester 在 氢溴酸 、 溶剂黄146 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 4.5h， 生成 Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-((R)-2,3-bis-benzyloxy-propoxy)-6-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of digalactosyl diacylglycerols and their structure–inhibitory activity on human lanosterol synthase

  摘要：

  Digalactosyl and monogalactocyl diacylglycerols (DGDG and MGDG), which were identified as anti-hyperlipemia active components in Colocasia esculenta (Taro), were synthesized. The inhibitory activity of DGDG, MGDG and related compounds on human lanosterol synthase was evaluated as anti-hyperlipemic activity. DGDG with two myristoyl groups at both sn-1 and sn-2 positions and with an oleoyl group at the sn-1 position showed the most potent activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.013