methyl [2-(trimethylsilyl)ethyl 3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate | 361192-87-2

• 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 3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate
• CAS: 361192-87-2
• 化学式: C₁₇H₃₀F₃NO₉Si
• 分子量: 477.507
• InChiKey: QPXDAKVQGVTDOU-ZIVBLGBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.88
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  154.78
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl [2-(trimethylsilyl)ethyl 3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氯化铝 、 三氟甲磺酸 、 二甲胺基甲硼烷 、 3 A molecular sieve 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 91.08h， 生成 methyl [2,4,7-tri-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)-5-trifluoroacetamido-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 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α,β-D-galacto-non-2-ulopyranosid]onate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到methyl [2-(trimethylsilyl)ethyl 3,5-dideoxy-5-trifluoroacetamido-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