6-O-benzyl-4-O-TES glucal | 322648-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-benzyl-4-O-TES glucal
• 英文别名: (2R,3S,4R)-2-(phenylmethoxymethyl)-3-triethylsilyloxy-3,4-dihydro-2H-pyran-4-ol
• CAS: 322648-62-4
• 化学式: C₁₉H₃₀O₄Si
• 分子量: 350.53
• InChiKey: PXPQHHOYBLFOHO-QRVBRYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-O-benzyl-4-O-TES glucal 在 sodium hydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 5.5h， 生成 (3aS,4R,6R,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3S,4R)-2-benzyloxymethyl-3-triethylsilanyloxy-3,4-dihydro-2H-pyran-4-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one
  参考文献：
  名称：

  Total Syntheses of Tumor-Related Antigens N3:  Probing the Feasibility Limits of the Glycal Assembly Method

  摘要：

  The total syntheses of two octasaccharide antigens isolated from human milk, 1 and 2, and their corresponding allyl glycosides, 3 and 4, have been achieved by utilizing the glycal method, Convergent assembly of the core hexasaccharides and concurrent introduction of two alpha -L-fucosyl moieties at the late stage of the syntheses provided these complex:carbohydrates in a concise manner. With synthetic material obtained, biological evaluations of these antigens as potential gastrointestinal cancer immunotherapeutic agents have been initiated.

  DOI：

  10.1021/ja0022730
• 作为产物：
  描述：

  1,5-脱水-2-脱氧-6-O-(苯基甲基)-D-阿拉伯-己-1-烯糖 在 吡啶 、 4-二甲氨基吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 6-O-benzyl-4-O-TES glucal
  参考文献：
  名称：

  Total Syntheses of Tumor-Related Antigens N3:  Probing the Feasibility Limits of the Glycal Assembly Method

  摘要：

  The total syntheses of two octasaccharide antigens isolated from human milk, 1 and 2, and their corresponding allyl glycosides, 3 and 4, have been achieved by utilizing the glycal method, Convergent assembly of the core hexasaccharides and concurrent introduction of two alpha -L-fucosyl moieties at the late stage of the syntheses provided these complex:carbohydrates in a concise manner. With synthetic material obtained, biological evaluations of these antigens as potential gastrointestinal cancer immunotherapeutic agents have been initiated.

  DOI：

  10.1021/ja0022730

文献信息

• Total Syntheses of Tumor-Related Antigens N3:  Probing the Feasibility Limits of the Glycal Assembly Method
  作者：Hyunjin M. Kim、In Jong Kim、Samuel J. Danishefsky

  DOI：10.1021/ja0022730

  日期：2001.1.1

  The total syntheses of two octasaccharide antigens isolated from human milk, 1 and 2, and their corresponding allyl glycosides, 3 and 4, have been achieved by utilizing the glycal method, Convergent assembly of the core hexasaccharides and concurrent introduction of two alpha -L-fucosyl moieties at the late stage of the syntheses provided these complex:carbohydrates in a concise manner. With synthetic material obtained, biological evaluations of these antigens as potential gastrointestinal cancer immunotherapeutic agents have been initiated.