benzyl 4'-(4-O-(methyl β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate | 869996-32-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: benzyl 4'-(4-O-(methyl β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate
• 英文别名: methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-hydroxy-4-(3-methyl-5-phenylmethoxy-4-phenylmethoxycarbonylphenoxy)carbonyl-5-pentadecylphenoxy]oxane-2-carboxylate
• CAS: 869996-32-7
• 化学式: C₅₁H₆₄O₁₃
• 分子量: 885.061
• InChiKey: ABDGPCVLTDHSKE-KXZWWNSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  64
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  188
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  benzyl 4'-(4-O-(methyl β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 24.0h， 以96%的产率得到CRM646-B
  参考文献：
  名称：

  Total Synthesis of CRM646-A and -B, Two Fungal Glucuronides with Potent Heparinase Inhibition Activities

  摘要：

  CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinolp-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approach involved construction of the phenol glucuronidic linkage, via coupling of the orsellinate derivative 27 with glucuronate bromide 7, before assembly of the phenolic ester linkage in the depside aglycone. Attempts via direct glycosylation of the depside aglycone derivatives were not successful.

  DOI：

  10.1021/jo051384k
• 作为产物：
  描述：

  2,4-二羟基-6-甲基苯甲酸 在 盐酸 、 4-二甲氨基吡啶 、 potassium carbonate 、 potassium hydrogencarbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 19.0h， 生成 benzyl 4'-(4-O-(methyl β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate
  参考文献：
  名称：

  Total Synthesis of CRM646-A and -B, Two Fungal Glucuronides with Potent Heparinase Inhibition Activities

  摘要：

  CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinolp-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approach involved construction of the phenol glucuronidic linkage, via coupling of the orsellinate derivative 27 with glucuronate bromide 7, before assembly of the phenolic ester linkage in the depside aglycone. Attempts via direct glycosylation of the depside aglycone derivatives were not successful.

  DOI：

  10.1021/jo051384k

文献信息

• Total Synthesis of CRM646-A and -B, Two Fungal Glucuronides with Potent Heparinase Inhibition Activities
  作者：Ping Wang、Zhaojun Zhang、Biao Yu

  DOI：10.1021/jo051384k

  日期：2005.10.1

  CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinolp-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approach involved construction of the phenol glucuronidic linkage, via coupling of the orsellinate derivative 27 with glucuronate bromide 7, before assembly of the phenolic ester linkage in the depside aglycone. Attempts via direct glycosylation of the depside aglycone derivatives were not successful.