methyl 2,3-bis-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside | 52430-30-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: methyl 2,3-bis-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-methoxy-5-(3,4,5-trimethoxybenzoyl)oxyoxan-4-yl] 3,4,5-trimethoxybenzoate
• CAS: 52430-30-5
• 化学式: C₂₇H₃₄O₁₄
• 分子量: 582.559
• InChiKey: ZMBWWDUTLZABJK-FEBXYHBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  167
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl 2,3-bis-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside 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， 生成 methyl 2,3,4,5-tetrakis(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside
  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
• 作为产物：
  描述：

  4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 在 palladium dihydroxide 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 环己烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 methyl 2,3-bis-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside
  参考文献：
  名称：

  A Rapid Total Synthesis of an Ellagitannin

  摘要：

  The ellagitannins are galloyl esters of glucose that contain at least one chiral biaryl (digalloyl) subunit. Included in this family are the tellimagrandins (1-3). The first asymmetric synthesis of (S)-4,4',5,5',6,6'-hexamethoxy-2,2'-diphenic acid, a ubiquitous subunit in ellagitannins, is reported by utilization of an intermolecular oxazoline-mediated asymmetric Ullmann coupling. Attachment of this acid to an appropriate glucose core resulted in the synthesis of an ellagitannin.

  DOI：

  10.1021/jo00088a046

文献信息

• Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B
  作者：Kazuma Shioe、Yusuke Sahara、Yoshikazu Horino、Takashi Harayama、Yasuo Takeuchi、Hitoshi Abe

  DOI：10.1016/j.tet.2011.01.004

  日期：2011.3

  Ellagitannins possess a wide range of biological activities and remarkable structural diversity, which commonly include an axially chiral biaryl unit. This paper describes syntheses of all-methylated versions of isorugosin B and rugosin B, which are regioisomeric, ellagitannin-related compounds. The key features of these syntheses involve the construction of an axially chiral biaryl function on a sugar moiety through a Pd-catalyzed intramolecular biaryl coupling reaction, Bringmann's atroposelective lactone opening reaction, and a two-step ester formation. This is the first synthetic approach for generating ellagitannins featuring a valoneoyl group. (C) 2011 Elsevier Ltd. All rights reserved.
• Studies Relevant to Ellagitannin Chemistry:  Highly Diastereoselective Intramolecular Biaryl Coupling in Bis(iodotrimethoxybenzoyl) Hexopyranose Derivatives
  作者：Dongcheng Dai、Olivier R. Martin

  DOI：10.1021/jo971722k

  日期：1998.10.1

  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.
• A Rapid Total Synthesis of an Ellagitannin
  作者：Todd D. Nelson、A. I. Meyers

  DOI：10.1021/jo00088a046

  日期：1994.5

  The ellagitannins are galloyl esters of glucose that contain at least one chiral biaryl (digalloyl) subunit. Included in this family are the tellimagrandins (1-3). The first asymmetric synthesis of (S)-4,4',5,5',6,6'-hexamethoxy-2,2'-diphenic acid, a ubiquitous subunit in ellagitannins, is reported by utilization of an intermolecular oxazoline-mediated asymmetric Ullmann coupling. Attachment of this acid to an appropriate glucose core resulted in the synthesis of an ellagitannin.