Methyl [2-(trimethylsilyl)ethyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid]onate | 361192-75-8

• 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-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-6-[(1R,2R)-1-acetyloxy-2-hydroxy-3-phenylmethoxypropyl]-2-(2-trimethylsilylethoxy)oxane-2-carboxylate
• CAS: 361192-75-8
• 化学式: C₂₈H₄₃NO₁₁Si
• 分子量: 597.735
• InChiKey: VGXVTWMTBIERKD-CWEZWLNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Methyl [2-(trimethylsilyl)ethyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 、 methyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-β-D-galacto-non-2-ulopyranosid)onate 在 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 0.33h， 以34%的产率得到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
• 作为产物：
  描述：

  Methyl [2-(trimethylsilyl)ethyl 5-acetamido-4,7-di-O-acetyl-8,9-O-benzylidene-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 在 三氯化铝 、 硼烷-三甲胺络合物 、 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到Methyl [2-(trimethylsilyl)ethyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
  参考文献：
  名称：

  A Novel Direct Glycosylation Approach for the Synthesis of Dimers ofN-Acetylneuraminic Acid

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19990401)5:4<1278::aid-chem1278>3.0.co;2-l