(2S,3S)-2,3-dimethoxy-1,4-butandiyl bis(4-O-benzylgallate) | 1160725-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-2,3-dimethoxy-1,4-butandiyl bis(4-O-benzylgallate)
• 英文别名: [(2S,3S)-4-(3,5-dihydroxy-4-phenylmethoxybenzoyl)oxy-2,3-dimethoxybutyl] 3,5-dihydroxy-4-phenylmethoxybenzoate
• CAS: 1160725-26-7
• 化学式: C₃₄H₃₄O₁₂
• 分子量: 634.637
• InChiKey: MNEQSPPBZPPHFE-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  170
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-dimethoxy-1,4-butandiyl bis(4-O-benzylgallate) 在 正丁胺 、 copper dichloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (2S,3S)-2,3-dimethoxy-1,4-butandiyl 5,5'-bis(benzyloxy)-4,4',6,6'-tetrahydroxy-1,1'-biphenyl-2,2'-dicarboxylate
  参考文献：
  名称：

  Synthesis of Chiral and Modifiable Hexahydroxydiphenoyl Compounds

  摘要：

  A reliable method for synthesizing each enantiomer of the hexahydroxydiphenoyl (HHDP) cornpounds has been developed. The synthesis involved atropselective construction of the aryl-aryl bond of the HHDP compounds. This construction relied on the CuCl2.n-BuNH2-mediated intramolecular coupling of bis (4-O-benzyl- gallate) on two simple chiral auxiliaries, both of which were derived from L-(+)-tartaric acid. The coupling reaction realized complete or near-perfect atropselectivity. The two auxiliaries induced opposite axial chirality despite their identical origin. The diastereoselectivities of these couplings were probably controlled kinetically. Modifications of the free phenolic hydroxy groups and the carbonyl groups in the resulting HHDP compounds demonstrated the potential derivatization of a wide variety of HHDP analogues.

  DOI：

  10.1021/jo201750d
• 作为产物：
  描述：

  (2S,3S)-2,3-dimethoxy-1,4-butanediol 在 盐酸 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 33.5h， 生成 (2S,3S)-2,3-dimethoxy-1,4-butandiyl bis(4-O-benzylgallate)
  参考文献：
  名称：

  Synthesis of Chiral and Modifiable Hexahydroxydiphenoyl Compounds

  摘要：

  A reliable method for synthesizing each enantiomer of the hexahydroxydiphenoyl (HHDP) cornpounds has been developed. The synthesis involved atropselective construction of the aryl-aryl bond of the HHDP compounds. This construction relied on the CuCl2.n-BuNH2-mediated intramolecular coupling of bis (4-O-benzyl- gallate) on two simple chiral auxiliaries, both of which were derived from L-(+)-tartaric acid. The coupling reaction realized complete or near-perfect atropselectivity. The two auxiliaries induced opposite axial chirality despite their identical origin. The diastereoselectivities of these couplings were probably controlled kinetically. Modifications of the free phenolic hydroxy groups and the carbonyl groups in the resulting HHDP compounds demonstrated the potential derivatization of a wide variety of HHDP analogues.

  DOI：

  10.1021/jo201750d

文献信息

• Synthesis of Chiral and Modifiable Hexahydroxydiphenoyl Compounds
  作者：Noriaki Asakura、Shohei Fujimoto、Naoki Michihata、Kentaro Nishii、Hiroshi Imagawa、Hidetoshi Yamada

  DOI：10.1021/jo201750d

  日期：2011.12.2

  A reliable method for synthesizing each enantiomer of the hexahydroxydiphenoyl (HHDP) cornpounds has been developed. The synthesis involved atropselective construction of the aryl-aryl bond of the HHDP compounds. This construction relied on the CuCl2.n-BuNH2-mediated intramolecular coupling of bis (4-O-benzyl- gallate) on two simple chiral auxiliaries, both of which were derived from L-(+)-tartaric acid. The coupling reaction realized complete or near-perfect atropselectivity. The two auxiliaries induced opposite axial chirality despite their identical origin. The diastereoselectivities of these couplings were probably controlled kinetically. Modifications of the free phenolic hydroxy groups and the carbonyl groups in the resulting HHDP compounds demonstrated the potential derivatization of a wide variety of HHDP analogues.