methyl [2-(trimethylsilyl)ethyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-D-glycero-α-D-galacto-non-2-ulopyranosid]onate | 361192-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [2-(trimethylsilyl)ethyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-6-[(1S,2R)-1-acetyloxy-2-[(2S,4S,5R,6R)-4-acetyloxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]-5-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxy-3-phenylmethoxypropyl]-2-(2-trimethylsilylethoxy)oxane-2-carboxylate
• CAS: 361192-80-5
• 化学式: C₄₈H₆₇F₃N₂O₂₃Si
• 分子量: 1125.14
• InChiKey: FCLXIDFRMGZWDE-LXPTWJANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  77
• 可旋转键数：
  33
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  315
• 氢给体数：
  2
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl [2-(trimethylsilyl)ethyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 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：

  methyl (2R,4S,5R,6R)-5-amino-4-hydroxy-2-methylsulfanyl-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 17.83h， 生成 methyl [2-(trimethylsilyl)ethyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-8-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
  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