2-(tetradecyl)hexadecyl 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-β-D-galactopyranoside | 653570-23-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(tetradecyl)hexadecyl 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-β-D-galactopyranoside
• 英文别名: 2-(tetradecyl)hexadecyl 2,4,6-tri-O-benzoyl-3-deoxy-3-C-(methoxycarbonylmethyl)-β-D-galactopyranoside；[(2R,3R,4S,5R,6R)-3,5-dibenzoyloxy-4-(2-methoxy-2-oxoethyl)-6-(2-tetradecylhexadecoxy)oxan-2-yl]methyl benzoate
• CAS: 653570-23-1
• 化学式: C₆₀H₈₈O₁₀
• 分子量: 969.353
• InChiKey: KXTCCKVEGARNKK-MRIGSKKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.8
• 重原子数：
  70
• 可旋转键数：
  42
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(tetradecyl)hexadecyl 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-β-D-galactopyranoside 在 sodium methylate 、 Amberlite IR-120(H+) 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以85%的产率得到2-(tetradecyl)hexadecyl 3-C-(carboxymethyl)-3-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and Selectin‐Blocking Activity of a Novel Analog of Sulfatide: 3‐C‐Carboxymethylgalactosyl Lipid

  摘要：

  The 3-C-carboxymethylgalactose derivative carrying the 2-(tetradecyl)hexadecyl residue, which was designed as a novel analog of sulfatide, was synthesized. A key intermediate, 3-C-carboxymethylgalactose, was prepared from the suitably protected galactose by Swern oxidation and Wittig-Horner carboxymethylenation, followed by stereoselective reduction of the double bond. The compound obtained showed much more potent activity as a selectin blocker than the 3-O-sulfogalactose derivative with 2-(tetradecyl)hexadecyl residue.

  DOI：

  10.1081/car-120026455
• 作为产物：
  描述：

  (2R,3S,5S,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-one 在 palladium on activated charcoal 吡啶 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 2-(tetradecyl)hexadecyl 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and Selectin‐Blocking Activity of a Novel Analog of Sulfatide: 3‐C‐Carboxymethylgalactosyl Lipid

  摘要：

  The 3-C-carboxymethylgalactose derivative carrying the 2-(tetradecyl)hexadecyl residue, which was designed as a novel analog of sulfatide, was synthesized. A key intermediate, 3-C-carboxymethylgalactose, was prepared from the suitably protected galactose by Swern oxidation and Wittig-Horner carboxymethylenation, followed by stereoselective reduction of the double bond. The compound obtained showed much more potent activity as a selectin blocker than the 3-O-sulfogalactose derivative with 2-(tetradecyl)hexadecyl residue.

  DOI：

  10.1081/car-120026455

文献信息

• Carboxymethylgalactose derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US06503885B1

  公开（公告）日：2003-01-07

  Carboxymethylgalactose derivatives represented by general formula (1); and salts thereof, which exhibit reactivity to selectins and are useful as inhibitors against selectin-related diseases such as various inflammations and cancerous metastasis; In said formula, R is a group rep resented by formula (1a), (1b) or (1c).

  通式（1）所代表的羧甲基半乳糖衍生物及其盐，具有对选择素的反应性，并可用作选择素相关疾病（如各种炎症和癌症转移）的抑制剂；在该式中，R是由式（1a）、（1b）或（1c）表示的基团。
• US6503885B1
  申请人：——

  公开号：US6503885B1

  公开（公告）日：2003-01-07
• Synthesis and Selectin‐Blocking Activity of a Novel Analog of Sulfatide: 3‐<i>C</i>‐Carboxymethylgalactosyl Lipid
  作者：Ai Ishihara、Hideharu Ishida、Takao Ikami、Noboru Tomiya、Hiromune Ando、Makoto Kiso

  DOI：10.1081/car-120026455

  日期：2003.12.31

  The 3-C-carboxymethylgalactose derivative carrying the 2-(tetradecyl)hexadecyl residue, which was designed as a novel analog of sulfatide, was synthesized. A key intermediate, 3-C-carboxymethylgalactose, was prepared from the suitably protected galactose by Swern oxidation and Wittig-Horner carboxymethylenation, followed by stereoselective reduction of the double bond. The compound obtained showed much more potent activity as a selectin blocker than the 3-O-sulfogalactose derivative with 2-(tetradecyl)hexadecyl residue.