(2R,3S,4R)-4-Azido-6-(2-hydroxy-ethoxy)-2-methyl-tetrahydro-pyran-3-ol | 611210-55-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-4-Azido-6-(2-hydroxy-ethoxy)-2-methyl-tetrahydro-pyran-3-ol
• CAS: 611210-55-0
• 化学式: C₈H₁₅N₃O₄
• 分子量: 217.225
• InChiKey: XXEFQNHUZPRHFR-DCDLSZRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.17
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  107.68
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-4-Azido-6-(2-hydroxy-ethoxy)-2-methyl-tetrahydro-pyran-3-ol 在 Lindlar's catalyst 咪唑 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 2-tert-butyldimethylsilyloxyethyl 2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

  摘要：

  The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5' side guanine of the 5'-GG-3' site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00820-2
• 作为产物：
  描述：

  methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 1.08h， 生成 (2R,3S,4R)-4-Azido-6-(2-hydroxy-ethoxy)-2-methyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

  摘要：

  The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5' side guanine of the 5'-GG-3' site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00820-2