Acetic acid (3aS,5R,6S,7S,7aS)-6-acetoxy-5-acetoxymethyl-2-trichloromethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-7-yl ester | 647021-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (3aS,5R,6S,7S,7aS)-6-acetoxy-5-acetoxymethyl-2-trichloromethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-7-yl ester
• 英文别名: [(3aS,5R,6S,7S,7aS)-6,7-diacetyloxy-2-(trichloromethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-5-yl]methyl acetate
• CAS: 647021-40-7
• 化学式: C₁₄H₁₆Cl₃NO₈
• 分子量: 432.642
• InChiKey: RZRRUSISTGOCFI-LVEVGFFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 Acetic acid (3aS,5R,6S,7S,7aS)-6-acetoxy-5-acetoxymethyl-2-trichloromethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-7-yl ester 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Trichloro-oxazolines as Activated Donors for Aminosugar Coupling

  摘要：

  [GRAPHICS]Starting from tri-O-acetyl-D-glucal, a combination of the Overman rearrangement and subsequent dihydroxylation produces a range of aminosugars. These can be activated by formation of the corresponding trichloro-oxazolines, which are excellent glycosyl donors as they form disaccharides with good (trans) stereoselectivity under mild conditions. Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions.

  DOI：

  10.1021/ol0359620
• 作为产物：
  描述：

  Acetic acid (3aS,5R,6S,7S,7aS)-6-acetoxy-5-acetoxymethyl-2-hydroxy-2-trichloromethyl-hexahydro-pyrano[3,2-d]oxazol-7-yl ester 在 三乙胺 、 甲基磺酸酐 作用下， 以 乙腈 为溶剂， 反应 1.33h， 生成 Acetic acid (3aS,5R,6S,7S,7aS)-6-acetoxy-5-acetoxymethyl-2-trichloromethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-7-yl ester
  参考文献：
  名称：

  Trichloro-oxazolines as Activated Donors for Aminosugar Coupling

  摘要：

  [GRAPHICS]Starting from tri-O-acetyl-D-glucal, a combination of the Overman rearrangement and subsequent dihydroxylation produces a range of aminosugars. These can be activated by formation of the corresponding trichloro-oxazolines, which are excellent glycosyl donors as they form disaccharides with good (trans) stereoselectivity under mild conditions. Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions.

  DOI：

  10.1021/ol0359620