(2S,3R)-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)-butyric acid 2-oxo-2-phenyl-ethyl ester | 188245-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,3R)-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)-butyric acid 2-oxo-2-phenyl-ethyl ester
• 英文别名: phenacyl (2S,3R)-3-[[(2S,4aR,6S,7R,8R,8aR)-7-acetamido-2-phenyl-8-(2,2,2-trichloroethanimidoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
• CAS: 188245-69-4
• 化学式: C₄₄H₄₂Cl₃N₃O₁₁
• 分子量: 895.19
• InChiKey: JEEJPFRALAAYRN-NQPULGCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  181
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S,3R)-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)-butyric acid 2-oxo-2-phenyl-ethyl ester 在 溶剂黄146 作用下， 以 水 为溶剂， 以87%的产率得到(2S,3R)-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)-butyric 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
• 作为产物：
  描述：

  N-[(2S,4aR,6S,7R,8R,8aR)-6,8-dihydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide 在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,3R)-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)-butyric 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

文献信息

• A novel glycosyl donor for the synthesis of cancer specific core 5 and sialyl core 5 as glycopeptide building blocks
  作者：Dongxu Qiu、R.Rao Koganty

  DOI：10.1016/s0040-4039(96)02490-2

  日期：1997.2

  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.