(3aS,4R,6S,7R,7aR)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-7-hydroxy-4-hydroxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one | 163129-59-7

• 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,7aR)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-7-hydroxy-4-hydroxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one
• CAS: 163129-59-7
• 化学式: C₂₇H₃₀O₁₀
• 分子量: 514.529
• InChiKey: HFFGVQDHSYGGIS-OFCSSXGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  122.14
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6S,7R,7aR)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-7-hydroxy-4-hydroxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one 在 甲醇 、 2-氯-1-甲基吡啶碘化物 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 46.5h， 生成 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl 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
• 作为产物：
  描述：

  (3aS,4R,6S,7R,7aR)-7-hydroxy-6-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (3aS,4R,6S,7R,7aR)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-7-hydroxy-4-hydroxymethyl-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

文献信息

• Major Simplifications in Oligosaccharide Syntheses Arising from a Solid-Phase Based Method: An Application to the Synthesis of the Lewis b Antigen
  作者：John T. Randolph、Kim F. McClure、Samuel J. Danishefsky

  DOI：10.1021/ja00126a012

  日期：1995.5

  Polymer bound glycals, upon activation by epoxidation, function as competent beta-glycosyl donors. The first glycal is linked through a silyl ether linker to a commercially available divinylbenzene polystyrene copolymer. At the end of the synthesis, soluble oligosaccharide is retrieved from the polymer by fluoridolysis. The method is self-corrective in that failed donors in a coupling step do not reemerge in the next cycle. The method is particularly powerful for creating branched sugars at C-2, a common branching site. An application of the solid phase method to a straightforward synthesis of the Lewis b antigen is described. The superiority of a diisopropylsilyl spacer relative to the previously employed diphenyl spacer is established (see compounds 4 and 5).