methyl 2-azido-6-bromo-2,6-dideoxy-3,4-O-methylidene-α-D-altropyranoside | 153165-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 2-azido-6-bromo-2,6-dideoxy-3,4-O-methylidene-α-D-altropyranoside
• CAS: 153165-78-7
• 化学式: C₁₀H₁₆BrN₃O₄
• 分子量: 322.159
• InChiKey: DEHNDIKOUYEMRO-DMAGGPPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-6-bromo-2,6-dideoxy-3,4-O-methylidene-α-D-altropyranoside 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以98%的产率得到methyl 2-azido-2,6-dideoxy-3,4-O-methylethylidene-α-D-arabino-hex-5-enopyranoside
  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：

  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