Pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside | 344550-91-0

• 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: Pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-[(4-methoxyphenoxy)methyl]-6-pent-4-enoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 344550-91-0
• 化学式: C₃₉H₄₄O₇
• 分子量: 624.774
• InChiKey: ADHHQOFEQUEURF-VZMNNQEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside 、 7-(1,3-dioxan-2-yl)-heptyl 2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-α-D-galactopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-α-D-galactopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-α-D-galactopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-... 在 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以69%的产率得到7-(1,3-dioxan-2-yl)-heptyl 2,3,4-tri-O-benzyl-6-O-(4-methoxyphenyl)-α-D-galactopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-α-D-galactopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-α-D-galactopyranosyl-(1->4)-2,3-di-O-benzyl-6-O...
  参考文献：
  名称：

  Synthesis of oligogalacturonates conjugated to BSA

  摘要：

  The synthesis of three oligogalacturonates with an aldehyde spacer attached at the reducing end is described. Trigalacturonates alpha-D-GalpA-(1-->4)-alpha-D-GalpA-(1-->4)-alpha-D-GalpA-(1-->O(CH2)(7)CHO and alpha-D-GalpA(Me)-(1-->4)-alpha-D-GalpA(Me)(1-->4)-alpha-D-GalpA(Me)-(1--> O(CH2)(7)CHO as well as hexagalacturonate alpha-D-GalpA-(1-->4)-[alpha-D-GalpA-(14)](4)-alpha-D-GalpA(1-->O(CH2)(7)CHO are prepared by stepwise coupling of galactose units followed by oxidation of the 6-positions. The alpha-linkages are formed by employing n-pentenyl galactosides as glycosyl donors and N-iodosuccinimide/triethylsilyl triflate as the promoter. Deprotection furnishes the three target oligogalacturonates, which are subsequently linked to bovine serum albumin by reductive amination. These neoglycoproteins will serve as immunogens for generation of new antibodies that can be used for localization and characterization of pectin in plants. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.06.012
• 作为产物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-yl ester 在 吡啶 、 甲醇 、 硫酸 、 sodium methylate 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.5h， 生成 Pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside
  参考文献：
  名称：

  A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid

  摘要：

  三半乳糖醛酸单甲酯1-3的合成被描述为向果胶低聚糖迈进的一般策略的一部分。所需的单体构建单元均从葡萄糖五乙酸酯大规模制备。糖基化反应是在葡萄糖糖基供体和受体之间使用n-戊烯糖基化技术进行的。所需的α-异头物的产率在50%到74%之间。由此获得的三半乳糖通过C-6位氧化。根据该位置的保护基团，氧化或者产生羧酸或相应的甲酯。因此，可以制备具有区域选择性引入甲酯的半乳糖醛酸低聚物。

  DOI：

  10.1039/b006981g

文献信息

• A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid
  作者：Mads H. Clausen、Malene R. Jørgensen、Jesper Thorsen、Robert Madsen

  DOI：10.1039/b006981g

  日期：——

  The synthesis of monomethyl-esterified trigalacturonans 1–3 is described as part of a general strategy towards pectic oligosaccharides. The necessary monomeric building blocks were all prepared on a large scale from galactose pentaacetate. The glycosylations were carried out between galactose glycosyl donors and acceptors using the n-pentenyl glycosylation technique. Yields of the desired α-anomers were in the 50 to 74% range. The trigalactans thus obtained were then subjected to oxidation at C-6. Depending on the protecting group at this position the oxidation either produced the carboxylic acid or the corresponding methyl ester. Hereby, oligomers of galacturonic acid can be prepared with methyl esters introduced in a regiocontrolled fashion.

  三半乳糖醛酸单甲酯1-3的合成被描述为向果胶低聚糖迈进的一般策略的一部分。所需的单体构建单元均从葡萄糖五乙酸酯大规模制备。糖基化反应是在葡萄糖糖基供体和受体之间使用n-戊烯糖基化技术进行的。所需的α-异头物的产率在50%到74%之间。由此获得的三半乳糖通过C-6位氧化。根据该位置的保护基团，氧化或者产生羧酸或相应的甲酯。因此，可以制备具有区域选择性引入甲酯的半乳糖醛酸低聚物。
• Synthesis of oligogalacturonates conjugated to BSA
  作者：Mads Clausen、Robert Madsen

  DOI：10.1016/j.carres.2004.06.012

  日期：2004.9

  The synthesis of three oligogalacturonates with an aldehyde spacer attached at the reducing end is described. Trigalacturonates alpha-D-GalpA-(1-->4)-alpha-D-GalpA-(1-->4)-alpha-D-GalpA-(1-->O(CH2)(7)CHO and alpha-D-GalpA(Me)-(1-->4)-alpha-D-GalpA(Me)(1-->4)-alpha-D-GalpA(Me)-(1--> O(CH2)(7)CHO as well as hexagalacturonate alpha-D-GalpA-(1-->4)-[alpha-D-GalpA-(14)](4)-alpha-D-GalpA(1-->O(CH2)(7)CHO are prepared by stepwise coupling of galactose units followed by oxidation of the 6-positions. The alpha-linkages are formed by employing n-pentenyl galactosides as glycosyl donors and N-iodosuccinimide/triethylsilyl triflate as the promoter. Deprotection furnishes the three target oligogalacturonates, which are subsequently linked to bovine serum albumin by reductive amination. These neoglycoproteins will serve as immunogens for generation of new antibodies that can be used for localization and characterization of pectin in plants. (C) 2004 Elsevier Ltd. All rights reserved.