(2R,3R,4S,5S,6R)-3-chloro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-amine | 1000845-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4S,5S,6R)-3-chloro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-amine
• CAS: 1000845-02-2
• 化学式: C₂₇H₃₀ClNO₄
• 分子量: 467.993
• InChiKey: BHTOUFUAVYODCH-IURCNINISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6R)-3-chloro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-amine 在 碳酸氢钠 、 magnesium 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 tert-butyl (2R,3R)-2-allyl-3-[(1R,2S,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl]aziridine-1-carboxylate
  参考文献：
  名称：

  从乙二醇合成手性氮丙啶：在哌啶-氮杂融合衍生物的合成中的应用

  摘要：

  衍生自缩醛的邻位氯胺已转化为相应的手性氮丙啶。尽管也可以形成四氢呋喃衍生物，但是已经开发了反应条件以仅产生叠氮基。一种氮丙啶类化合物与用于合成抗病毒剂扎那米韦的先进中间体的合成中的化合物密切相关。此外，氮丙啶中的一种已被转化为哌啶-氮杂卓稠合的衍生物。

  DOI：

  10.1002/ejoc.201700624
• 作为产物：
  描述：

  N-[(2S,3R,4S,5S,6R)-3-chloro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetamide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 (2R,3R,4S,5S,6R)-3-chloro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-amine
  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

文献信息

• New Method for Chloroamidation of Olefins. Application in the Synthesis of <i>N</i>-Glycopeptides and Anticancer Agents
  作者：Girish K. Rawal、Amit Kumar、Urmila Tawar、Yashwant D. Vankar

  DOI：10.1021/ol702097q

  日期：2007.12.1

  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.
• Synthesis of Chiral Aziridines from Glycals: Application in the Synthesis of a Piperidine-Azepine Fused Derivative
  作者：Rima Thakur、Girish K. Rawal、Yashwant D. Vankar

  DOI：10.1002/ejoc.201700624

  日期：2017.8.10

  Vicinal chloroamines derived from glycals have been converted into the corresponding chiral aziridines. Although the formation of a tetrahydrofuran derivative was also possible, reaction conditions have been developed to give exclusively the azirdines. One of the aziridines closely relates to a compound used in the synthesis of an advanced intermediate en route to Zanamivir, an antiviral agent. Further

  衍生自缩醛的邻位氯胺已转化为相应的手性氮丙啶。尽管也可以形成四氢呋喃衍生物，但是已经开发了反应条件以仅产生叠氮基。一种氮丙啶类化合物与用于合成抗病毒剂扎那米韦的先进中间体的合成中的化合物密切相关。此外，氮丙啶中的一种已被转化为哌啶-氮杂卓稠合的衍生物。