1,2:3,4-di-O-isopropylidene-6-O-3,4,5-tri-methoxybenzoyl-D-galactopyranose

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 1,2:3,4-di-O-isopropylidene-6-O-3,4,5-tri-methoxybenzoyl-D-galactopyranose
• 英文别名: [(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl 3,4,5-trimethoxybenzoate
• 化学式: C₂₂H₃₀O₁₀
• 分子量: 454.474
• InChiKey: JXZOFGAVIGQLGP-GIYWUFHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-碘-3,4,5-三甲氧基苯甲酸 在 4-二甲氨基吡啶 、 铜 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1,2:3,4-di-O-isopropylidene-6-O-3,4,5-tri-methoxybenzoyl-D-galactopyranose
  参考文献：
  名称：

  Studies Relevant to Ellagitannin Chemistry:  Highly Diastereoselective Intramolecular Biaryl Coupling in Bis(iodotrimethoxybenzoyl) Hexopyranose Derivatives

  摘要：

  Internal biaryl coupling reactions of carbohydrate derivatives carrying two 2-iodo-3,4,5-trimethoxybenzoyl groups under Ullmann conditions were investigated. With substituents at positions 2,3 or 4,6 of a D-glucopyranoside, 2,3 of a D-mannopyranoside, and 3,4 of a D-galactopyranoside, the coupling was found to proceed with a very high degree of stereoselectivity, leading exclusively to the (S)-epimer of the resulting hexamethoxydiphenoyl residue from the D-gluco and D-galacto substrates, and to the (R)-epimer from the D-manno substrate. With substituents at positions 2,4 of D-glucopyranose derivatives in the C-1(4) conformation and at positions 5,6 of a D-glucofuranose derivative, the coupling proceeded efficiently but with modest stereoselectivity. Some deiodinated starting material was formed as a byproduct in all reactions. These results are relevant to ellagitannin chemistry in that they provide further understanding of the structural requirements for highly diastereoselective biaryl coupling within carbohydrate units. In addition, the efficient, complementary reactions of the D-manno and D-galacto substrates provide a method for the enantioselective synthesis of hexamethoxydiphenoic acid derivatives.

  DOI：

  10.1021/jo971722k

文献信息

• An Approach to the Synthesis of Electron-Rich and Hindered Esters and Its Application to the Synthesis of Acteoside
  作者：Xiaojuan Zhang、Yutong Yang、Fuye Wang、Zhengbing Zhou、Hongbin Zhang、Yugen Zhu

  DOI：10.1021/acs.orglett.1c03528

  日期：2021.12.3

  distributed in natural products and play a central role in bioactivities. Herein, we disclose an efficient, mild, and general esterification approach to the synthesis of these esters by employing gold(I)-catalyzed acylation reaction with alkyne-tethered mixed anhydrides and alcohols. This method can be applied to ester-bond formation in complex substrates and facilitates efficient synthesis of acteoside

  富含电子的酯类普遍存在于天然产物中，并在生物活性中发挥核心作用。在此，我们公开了一种有效、温和且通用的酯化方法，通过采用金 (I) 催化的酰化反应与炔烃连接的混合酸酐和醇来合成这些酯。该方法可应用于复杂底物的酯键形成，并有助于高效合成属于苯乙醇苷家族的acteoside，具有广泛的生物活性。