4-acetoxy-2-[3-acetoxy-4-(7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3,4-dihydro-2H-pyran-2-ylmethoxy]-5-acetylamino-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 197518-61-9

• 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)-3,4-dihydro-2H-pyran-2-ylmethoxy]-5-acetylamino-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 197518-61-9
• 化学式: C₃₉H₅₁NO₂₅
• 分子量: 933.826
• InChiKey: PYSDDWYWEHFHNU-XWCKMSFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.12
• 重原子数：
  65.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  321.18
• 氢给体数：
  1.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  4-acetoxy-2-[3-acetoxy-4-(7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3,4-dihydro-2H-pyran-2-ylmethoxy]-5-acetylamino-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium azide 、 ammonium cerium(IV) nitrate 、 苯硫酚 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 12.17h， 生成
  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：

  Acetic acid (3aS,4R,6R,7R,7aS)-4-acetoxymethyl-6-((2R,3R,4R)-3-acetoxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxy)-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 在 TMSTf 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 7.0h， 生成 4-acetoxy-2-[3-acetoxy-4-(7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3,4-dihydro-2H-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