methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside | 53437-74-4

• 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: methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside
• 英文别名: [(2S,3S,4S,5S,6S)-5-azido-2-(bromomethyl)-4-hydroxy-6-methoxyoxan-3-yl] benzoate
• CAS: 53437-74-4
• 化学式: C₁₄H₁₆BrN₃O₅
• 分子量: 386.202
• InChiKey: QWCGLICGLBJQJF-LARJDALCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113.75
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside 在 硫酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 methyl 2-azido-6-bromo-2,6-dideoxy-3,4-O-methylidene-α-D-altropyranoside
  参考文献：
  名称：

  Enantiospecific synthesis and biological evaluation of seco analogues of antitumor amaryllidaceae alkaloids

  摘要：

  Some ''seco'' analogues of Amaryllidaceae alkaloids narciclasine and lycoricidine have been prepared in enantiomerically pure form from D-glucose using Ferrier carbocyclization as the key step. N-acylation of the resulting amines 21, 22, 25 and 26 with several aromatic acids led to amides 31-34 structurally related to narciclasine and lycoricidine. These seco analogues are devoided of biological activity.

  DOI：

  10.1016/s0040-4020(01)87223-9
• 作为产物：
  描述：

  2-azido-2-deoxy-4,6-O-(phenylmethylene)methyl-α-D-altropyranoside 在 N-溴代丁二酰亚胺(NBS) 、 calcium carbonate 作用下， 以 四氯化碳 为溶剂， 以87%的产率得到methyl 2-azido-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-altropyranoside
  参考文献：
  名称：

  Enantiospecific synthesis and biological evaluation of seco analogues of antitumor amaryllidaceae alkaloids

  摘要：

  Some ''seco'' analogues of Amaryllidaceae alkaloids narciclasine and lycoricidine have been prepared in enantiomerically pure form from D-glucose using Ferrier carbocyclization as the key step. N-acylation of the resulting amines 21, 22, 25 and 26 with several aromatic acids led to amides 31-34 structurally related to narciclasine and lycoricidine. These seco analogues are devoided of biological activity.

  DOI：

  10.1016/s0040-4020(01)87223-9

文献信息

• Chretien, Francoise; Khaldi, Mustapha; Chapleur, Yves, Synthetic Communications, 1990, vol. 20, # 11, p. 1589 - 1596
  作者：Chretien, Francoise、Khaldi, Mustapha、Chapleur, Yves

  DOI：——

  日期：——
• CHRETIEN, FRANCOISE;KHALDI, MUSTAPHA;CHAPLEUR, YVES, SYNTH. COMMUN., 20,(1990) N1, C. 1589-1596
  作者：CHRETIEN, FRANCOISE、KHALDI, MUSTAPHA、CHAPLEUR, YVES

  DOI：——

  日期：——
• HENDRY, DAVID;HOUGH, LESLIE;RICHARDSON, ANTHONY C., TETRAHEDRON, 44,(1988) N 19, C. 6153-6168
  作者：HENDRY, DAVID、HOUGH, LESLIE、RICHARDSON, ANTHONY C.

  DOI：——

  日期：——