(S)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester | 188245-74-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester
• 英文别名: phenacyl (2S)-3-[[(3aR,4R,6S,7R,7aR)-7-acetamido-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 188245-74-1
• 化学式: C₃₇H₄₀N₂O₁₁
• 分子量: 688.731
• InChiKey: AQRSEJJFBGZCHN-GBJHZFISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  168
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (S)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester 在 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 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：

  N-(9-芴甲氧羰基)-L-丝氨酸苯甲酰甲酯 在 三氟化硼乙醚 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (S)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-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

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.