[(2R,3S,4S,5R,6R)-6-acetamido-3,4-diacetyloxy-5-chlorooxan-2-yl]methyl acetate | 1000844-96-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4S,5R,6R)-6-acetamido-3,4-diacetyloxy-5-chlorooxan-2-yl]methyl acetate
• CAS: 1000844-96-1
• 化学式: C₁₄H₂₀ClNO₈
• 分子量: 365.768
• InChiKey: SKOMUXDFQHBONR-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙腈 、 D-三乙酰半乳糖烯 在 草酰氯 、 silver nitrate 作用下， 以80%的产率得到Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-acetylamino-5-chloro-tetrahydro-pyran-4-yl ester
  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