Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-[(2R,3S,4S,5R,6S)-2-acetoxymethyl-4,5-bis-benzyloxy-6-(7-[1,3]dioxan-2-yl-heptyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester | 783367-47-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-[(2R,3S,4S,5R,6S)-2-acetoxymethyl-4,5-bis-benzyloxy-6-(7-[1,3]dioxan-2-yl-heptyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester
• CAS: 783367-47-5
• 化学式: C₅₇H₇₁ClO₁₆
• 分子量: 1047.63
• InChiKey: FNSNJAPYCLRUEZ-MVCNSXIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.56
• 重原子数：
  74.0
• 可旋转键数：
  29.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  171.2
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-[(2R,3S,4S,5R,6S)-2-acetoxymethyl-4,5-bis-benzyloxy-6-(7-[1,3]dioxan-2-yl-heptyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester 在 四丁基碘化铵 、 碳酸氢钠 、 硫脲 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以78%的产率得到Acetic acid (2R,3S,4S,5R,6S)-3-((2R,3R,4S,5S,6R)-6-acetoxymethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-(7-[1,3]dioxan-2-yl-heptyloxy)-tetrahydro-pyran-2-ylmethyl ester
  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：

  pent-4-enyl 6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 溴 、 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， 生成 Chloro-acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-[(2R,3S,4S,5R,6S)-2-acetoxymethyl-4,5-bis-benzyloxy-6-(7-[1,3]dioxan-2-yl-heptyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-tetrahydro-pyran-3-yl ester
  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