methyl 2-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]acetate | 197243-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]acetate
• CAS: 197243-28-0
• 化学式: C₁₄H₂₈O₇Si
• 分子量: 336.458
• InChiKey: KWILMONHXAIPHH-NRFQWKTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.04
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]acetate 在 吡啶 、 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 18.0h， 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
• 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 氢气 、 sodium methylate 、 溶剂黄146 作用下， 反应 7.0h， 生成 methyl 2-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]acetate
  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

• Synthesis of the 3′-C-carboxymethyl Lewis X derivative: a novel selectin blocker
  作者：Hideharu Ishida、Hiroyuki Hosokawa、Hirosato Kondo、Makoto Kiso、Akira Hasegawa

  DOI：10.1016/s0008-6215(97)00156-0

  日期：1997.9

  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.