(3R,15S,21R)-21-benzyloxy-15-(2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-3-(4-methoxybenzyloxy)docosanoic acid | 725723-95-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,15S,21R)-21-benzyloxy-15-(2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-3-(4-methoxybenzyloxy)docosanoic acid
• 英文别名: (3R,15S,21R)-15-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-3-[(4-methoxyphenyl)methoxy]-21-phenylmethoxydocosanoic acid
• CAS: 725723-95-5
• 化学式: C₆₄H₈₆O₁₁
• 分子量: 1031.38
• InChiKey: JNJLMDXDLVDNOJ-FDTDTWKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  75
• 可旋转键数：
  39
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3R,15S,21R)-21-benzyloxy-15-(2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-3-(4-methoxybenzyloxy)docosanoic acid 在 2-chloro-1,3-dimethyl-2-imidazolinium chloride 、 sodium hydride 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 以35%的产率得到(1R,3S,15R,20R,21R,22S,23R,24R,26S,38R,43R,44R,45S,46R)-15,38-bis[(4-methoxyphenyl)methoxy]-21,22,23,44,45,46-hexakis(phenylmethoxy)-3,26-bis[(6R)-6-phenylmethoxyheptyl]-2,18,25,41,47,48-hexaoxatricyclo[41.3.1.120,24]octatetracontane-17,40-dione
  参考文献：
  名称：

  Synthetic Studies on Macroviracin A:  A Rapid Construction of C₄₂ Macrocyclic Dilactone Corresponding to the Core

  摘要：

  The C-2-symmetric macrodiolide core 2 of an antiviral agent, macroviracin A (1), was constructed in a single step by the intermolecular macrodimerization of C-22-hydroxy carboxylic acid 3 with 2-chloro-1,3-dimethylimidazolinium chloride and DMAP in the presence of sodium hydride (NaH). The use of potassium hydride instead of NaH caused the intramolecular cyclization, predominantly providing the corresponding monomer 26. The acid 3 was synthesized through a series of reactions such as the coupling reaction of acetylene 5 and oxirane 6, stereoselective glycosidation with the trichloroacetimidate method, and Jones oxidation.

  DOI：

  10.1021/jo0496392
• 作为产物：
  描述：

  (2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docosan-8-ol 在 sodium hydroxide 、 jones reagent 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 9.16h， 生成 (3R,15S,21R)-21-benzyloxy-15-(2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-3-(4-methoxybenzyloxy)docosanoic acid
  参考文献：
  名称：

  Synthetic Studies on Macroviracin A:  A Rapid Construction of C₄₂ Macrocyclic Dilactone Corresponding to the Core

  摘要：

  The C-2-symmetric macrodiolide core 2 of an antiviral agent, macroviracin A (1), was constructed in a single step by the intermolecular macrodimerization of C-22-hydroxy carboxylic acid 3 with 2-chloro-1,3-dimethylimidazolinium chloride and DMAP in the presence of sodium hydride (NaH). The use of potassium hydride instead of NaH caused the intramolecular cyclization, predominantly providing the corresponding monomer 26. The acid 3 was synthesized through a series of reactions such as the coupling reaction of acetylene 5 and oxirane 6, stereoselective glycosidation with the trichloroacetimidate method, and Jones oxidation.

  DOI：

  10.1021/jo0496392

文献信息

• Synthetic Studies on Macroviracin A:  A Rapid Construction of C₄₂ Macrocyclic Dilactone Corresponding to the Core
  作者：Shunya Takahashi、Kazunori Souma、Ruri Hashimoto、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1021/jo0496392

  日期：2004.6.1

  The C-2-symmetric macrodiolide core 2 of an antiviral agent, macroviracin A (1), was constructed in a single step by the intermolecular macrodimerization of C-22-hydroxy carboxylic acid 3 with 2-chloro-1,3-dimethylimidazolinium chloride and DMAP in the presence of sodium hydride (NaH). The use of potassium hydride instead of NaH caused the intramolecular cyclization, predominantly providing the corresponding monomer 26. The acid 3 was synthesized through a series of reactions such as the coupling reaction of acetylene 5 and oxirane 6, stereoselective glycosidation with the trichloroacetimidate method, and Jones oxidation.