2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate | 197243-30-4

• 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: 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate
• 英文别名: [(2R,3R,4S,5R,6R)-3,5-dibenzoyloxy-4-(2-methoxy-2-oxoethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 197243-30-4
• 化学式: C₃₂H₂₈Cl₃NO₁₀
• 分子量: 692.934
• InChiKey: CPEWUEFWXXWOBM-IUOGNAKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate 在 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 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 、 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 25.0h， 生成 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate
  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