(2R,3S,4R)-3-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-[tri(propan-2-yl)silyloxymethyl]-3,4-dihydro-2H-pyran-4-ol | 210427-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-3-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-[tri(propan-2-yl)silyloxymethyl]-3,4-dihydro-2H-pyran-4-ol
• CAS: 210427-06-8
• 化学式: C₄₂H₅₈O₈Si
• 分子量: 719.003
• InChiKey: FJLPTIBAFTZEEV-SJFPFTSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-3-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-[tri(propan-2-yl)silyloxymethyl]-3,4-dihydro-2H-pyran-4-ol 在 iodonium(di-γ-collidine) perchlorate 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成
  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：

  6-O-triisopropylsilyl-3-O-triphenylsilyl glucal 在 tin(ll) chloride 甲醇 、 silver perchlorate 、 potassium carbonate 、 Di-tert-butylpyridine 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 42.0h， 生成 (2R,3S,4R)-3-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-[tri(propan-2-yl)silyloxymethyl]-3,4-dihydro-2H-pyran-4-ol
  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.