(2R,3S,5S,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-one | 197243-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,5S,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-one
• CAS: 197243-26-8
• 化学式: C₃₂H₄₀O₆Si
• 分子量: 548.751
• InChiKey: KWQDOXQMORJRRZ-IMRLWEKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,5S,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-one 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 2.0h， 生成 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-D-galactopyranose
  参考文献：
  名称：

  Synthesis of the 3′-C-carboxymethyl Lewis X derivative: a novel selectin blocker

  摘要：

  The 3'-C-carboxymethyl Le(x) derivative carrying the 2-(tetradecyl)hexadecyl residue was synthesized by employing 3'-C-carboxymethyl galactose as a key intermediate, which 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 sialyl Lex derivative with 2-(tetradecyl)hexadecyl residue. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00156-0
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2R,3S,5S,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-one
  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