methyl (2S,4S,5R,6R)-4-acetyloxy-2-[(1S,2R)-1-acetyloxy-1-[(2R,3R,4S,6R)-4-acetyloxy-3-(diacetylamino)-6-methoxycarbonyl-6-(2-trimethylsilylethoxy)oxan-2-yl]-3-phenylmethoxypropan-2-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]-5-[(2,2,2-trifluoroacetyl)amino]oxane-2-carboxylate | 361192-82-7

• 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: methyl (2S,4S,5R,6R)-4-acetyloxy-2-[(1S,2R)-1-acetyloxy-1-[(2R,3R,4S,6R)-4-acetyloxy-3-(diacetylamino)-6-methoxycarbonyl-6-(2-trimethylsilylethoxy)oxan-2-yl]-3-phenylmethoxypropan-2-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]-5-[(2,2,2-trifluoroacetyl)amino]oxane-2-carboxylate
• CAS: 361192-82-7
• 化学式: C₅₀H₆₉F₃N₂O₂₄Si
• 分子量: 1167.18
• InChiKey: WRJZPCLLYGECRL-MJRNSZEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  80
• 可旋转键数：
  33
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  323
• 氢给体数：
  1
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl (2S,4S,5R,6R)-4-acetyloxy-2-[(1S,2R)-1-acetyloxy-1-[(2R,3R,4S,6R)-4-acetyloxy-3-(diacetylamino)-6-methoxycarbonyl-6-(2-trimethylsilylethoxy)oxan-2-yl]-3-phenylmethoxypropan-2-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]-5-[(2,2,2-trifluoroacetyl)amino]oxane-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 88.0h， 生成 2-(trimethylsilyl)ethyl 5-acetamido-8-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-9-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid disodium salt
  参考文献：
  名称：

  A Stereoselective Approach for the Synthesis of α-Sialosides

  摘要：

  A highly efficient synthesis of the human melanoma associated antigen GD(3) derivative has been described. A key feature of the synthetic approach was the use of sialyl donors that were protected with a C-5 trifluoroacetamide moiety. These sialyl donors gave high yields and excellent alpha-anomeric selectivities in direct glycosylations with a wide variety of glycosyl acceptors ranging from C-8 hydroxyls of sialic acids and C-3 hydroxyls of galactosides to reactive primary alcohols.

  DOI：

  10.1021/jo010345f
• 作为产物：
  描述：

  在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 16.08h， 生成 methyl (2S,4S,5R,6R)-4-acetyloxy-2-[(1S,2R)-1-acetyloxy-1-[(2R,3R,4S,6R)-4-acetyloxy-3-(diacetylamino)-6-methoxycarbonyl-6-(2-trimethylsilylethoxy)oxan-2-yl]-3-phenylmethoxypropan-2-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]-5-[(2,2,2-trifluoroacetyl)amino]oxane-2-carboxylate
  参考文献：
  名称：

  A Stereoselective Approach for the Synthesis of α-Sialosides

  摘要：

  A highly efficient synthesis of the human melanoma associated antigen GD(3) derivative has been described. A key feature of the synthetic approach was the use of sialyl donors that were protected with a C-5 trifluoroacetamide moiety. These sialyl donors gave high yields and excellent alpha-anomeric selectivities in direct glycosylations with a wide variety of glycosyl acceptors ranging from C-8 hydroxyls of sialic acids and C-3 hydroxyls of galactosides to reactive primary alcohols.

  DOI：

  10.1021/jo010345f