tert-butyl N4-((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-chlorotetrahydro-2H-pyran-2-yl)-N2-(tert-butoxycarbonyl)-L-asparaginate | 1000845-07-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl N4-((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-chlorotetrahydro-2H-pyran-2-yl)-N2-(tert-butoxycarbonyl)-L-asparaginate
• CAS: 1000845-07-7
• 化学式: C₄₀H₅₁ClN₂O₉
• 分子量: 739.306
• InChiKey: KWIIYVYDKKPOPT-XATJWUCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  52.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  130.65
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N4-((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-chlorotetrahydro-2H-pyran-2-yl)-N2-(tert-butoxycarbonyl)-L-asparaginate 在 偶氮二异丁腈 、 三丁基氯化锡 、 sodium cyanoborohydride 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以82%的产率得到
  参考文献：
  名称：

  New Method for Chloroamidation of Olefins. Application in the Synthesis of N-Glycopeptides and Anticancer Agents

  摘要：

  Chloroamidation of olefins using a new reagent system (COCl)(2)-AgNO3-CH3CN was observed. Various glycals with this reagent system produce 2-chloro-1-acetamido sugars in good yields which, in turn, were converted to free amino derivatives and various glycopeptides. The acetamido sugar derivatives and free amines were found to be promising anticancer agents against the U-87 malignant glyoma (a brain tumor) cell line with IC-50 = 1 nm-22 mu M, and they were found to be far less cytotoxic against a normal human embryonic kidney cell line.

  DOI：

  10.1021/ol702097q
• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-3-chloro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-amine 、 N-叔丁氧羰基-L-天冬氨酸 1-叔丁酯 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以72%的产率得到tert-butyl N4-((2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-chlorotetrahydro-2H-pyran-2-yl)-N2-(tert-butoxycarbonyl)-L-asparaginate
  参考文献：
  名称：

  New Method for Chloroamidation of Olefins. Application in the Synthesis of N-Glycopeptides and Anticancer Agents

  摘要：

  Chloroamidation of olefins using a new reagent system (COCl)(2)-AgNO3-CH3CN was observed. Various glycals with this reagent system produce 2-chloro-1-acetamido sugars in good yields which, in turn, were converted to free amino derivatives and various glycopeptides. The acetamido sugar derivatives and free amines were found to be promising anticancer agents against the U-87 malignant glyoma (a brain tumor) cell line with IC-50 = 1 nm-22 mu M, and they were found to be far less cytotoxic against a normal human embryonic kidney cell line.

  DOI：

  10.1021/ol702097q