(3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4R)-2-benzyloxymethyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-3-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one | 322648-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4R)-2-benzyloxymethyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-3-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one
• CAS: 322648-47-5
• 化学式: C₄₀H₅₀O₁₀Si
• 分子量: 718.917
• InChiKey: WJTHOIWDJDONQH-XMYVNOLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  51.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  100.14
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4R)-2-benzyloxymethyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-3-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 N-[(2S,3R,4R,5R,6R)-5-[[(3aS,4R,6S,7R,7aS)-2-oxo-7-phenylmethoxy-4-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-ethylsulfanyl-6-(phenylmethoxymethyl)-4-triethylsilyloxyoxan-3-yl]benzenesulfonamide
  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：

  溴甲苯 、 (3aS,4R,6S,7R,7aR)-7-hydroxy-4-(phenylmethoxymethyl)-6-[[(2R,3R,4R)-2-(phenylmethoxymethyl)-4-triethylsilyloxy-3,4-dihydro-2H-pyran-3-yl]oxy]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以93%的产率得到(3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4R)-2-benzyloxymethyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-3-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