Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3S,4R)-3-hydroxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester | 210427-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3S,4R)-3-hydroxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester
• CAS: 210427-11-5
• 化学式: C₄₂H₅₆O₉Si
• 分子量: 732.987
• InChiKey: CEIYEIWOCQPJOS-OMHIFQTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.98
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101.91
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3S,4R)-3-hydroxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester 在 sodium hydride 、 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 3.75h， 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-(三异丙基硅基)-D-葡萄烯糖 、 fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose 在 tin(ll) chloride silver perchlorate 、 Di-tert-butylpyridine 作用下， 以 乙醚 为溶剂， 以55%的产率得到Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3S,4R)-3-hydroxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester
  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