(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester | 188245-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester
• CAS: 188245-70-7
• 化学式: C₄₁H₄₀N₂O₁₁
• 分子量: 736.775
• InChiKey: JRKXVEHCSHWDCT-YDLKUKBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  54.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  167.95
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 、 (S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到
  参考文献：
  名称：

  A novel glycosyl donor for the synthesis of cancer specific core 5 and sialyl core 5 as glycopeptide building blocks

  摘要：

  Trichloroacetimidate at 1 and 3 position of 4,6-benzylidenyl N-acetylgalactosamine serves as a leaving group for glycosylation and a selective and acid sensitive protecting group respectively. This versatile donor, while forming exclusive alpha-glycoside with serine/threonine, serves as a fascile precursor to 3-OH which can be generated in acid medium without affecting 4,6-acetal protecting group or the protecting groups of serine/threonine. Synthesis of cancer associated carbohydrate Core 5 and its sialylated analog are accomplished through the use of this donor. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02490-2
• 作为产物：
  描述：

  (S)-3-[(2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-2-phenyl-8-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester 在 溶剂黄146 作用下， 以 水 为溶剂， 以69%的产率得到(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester
  参考文献：
  名称：

  A novel glycosyl donor for the synthesis of cancer specific core 5 and sialyl core 5 as glycopeptide building blocks

  摘要：

  Trichloroacetimidate at 1 and 3 position of 4,6-benzylidenyl N-acetylgalactosamine serves as a leaving group for glycosylation and a selective and acid sensitive protecting group respectively. This versatile donor, while forming exclusive alpha-glycoside with serine/threonine, serves as a fascile precursor to 3-OH which can be generated in acid medium without affecting 4,6-acetal protecting group or the protecting groups of serine/threonine. Synthesis of cancer associated carbohydrate Core 5 and its sialylated analog are accomplished through the use of this donor. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02490-2