4-acetoxy-2-[3-acetoxy-4-(7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-5-azido-6-bromo-tetrahydro-pyran-2-ylmethoxy]-5-acetylamino-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 197518-67-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetoxy-2-[3-acetoxy-4-(7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-5-azido-6-bromo-tetrahydro-pyran-2-ylmethoxy]-5-acetylamino-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 197518-67-5
• 化学式: C₃₉H₅₁BrN₄O₂₅
• 分子量: 1055.75
• InChiKey: KYIPAFWXJRUCHH-BCHMFOOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  69.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  369.94
• 氢给体数：
  1.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  N-[(9H-芴-9-甲氧基)羰基]-L-苏氨酸苯基甲酯 、 4-acetoxy-2-[3-acetoxy-4-(7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-5-azido-6-bromo-tetrahydro-pyran-2-ylmethoxy]-5-acetylamino-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到
  参考文献：
  名称：

  A Broadly Applicable Method for the Efficient Synthesis of α-O-Linked Glycopeptides and Clustered Sialic Acid Residues

  摘要：

  The total syntheses of complex sialylated cell-surface antigens have been accomplished. The target systems include 2.3-STF, STn, 2,6-STF, and glycophorin antigens. In addition,an alpha-O-linked serine glycoside of an entire Lewis blood group (Y) antigen has been assembled.

  DOI：

  10.1021/ja9833265
• 作为产物：
  描述：

  在 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以75%的产率得到4-acetoxy-2-[3-acetoxy-4-(7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-5-azido-6-bromo-tetrahydro-pyran-2-ylmethoxy]-5-acetylamino-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A Broadly Applicable Method for the Efficient Synthesis of α-O-Linked Glycopeptides and Clustered Sialic Acid Residues

  摘要：

  The total syntheses of complex sialylated cell-surface antigens have been accomplished. The target systems include 2.3-STF, STn, 2,6-STF, and glycophorin antigens. In addition,an alpha-O-linked serine glycoside of an entire Lewis blood group (Y) antigen has been assembled.

  DOI：

  10.1021/ja9833265