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 | 188245-67-2

• 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: 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
• 英文别名: [(2S,4aR,6R,7R,8R,8aR)-7-acetamido-2-phenyl-6-(2,2,2-trichloroethanimidoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2,2,2-trichloroethanimidate
• CAS: 188245-67-2
• 化学式: C₁₉H₁₉Cl₆N₃O₆
• 分子量: 598.094
• InChiKey: AAOQAFHNALRZCD-JSLGZRHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

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 在 吡啶 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  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：

  三氯乙腈 、 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 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到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
  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.