N-[(2S,3S,4S,5R,6R)-5-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-4-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide | 322648-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3S,4S,5R,6R)-5-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-4-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide
• CAS: 322648-48-6
• 化学式: C₄₆H₅₆INO₁₂SSi
• 分子量: 1002.01
• InChiKey: CEDFIRPWSOLVLI-JXBUQBRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  62.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  146.31
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  乙硫醇 、 N-[(2S,3S,4S,5R,6R)-5-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-4-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以90%的产率得到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：

  (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 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成 N-[(2S,3S,4S,5R,6R)-5-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-4-triethylsilanyloxy-tetrahydro-pyran-2-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