2-tert-butyldimethylsilyloxyethyl 3-azido-2,3,6-trideoxy-β-D-arabino-hexopyranoside | 611210-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-tert-butyldimethylsilyloxyethyl 3-azido-2,3,6-trideoxy-β-D-arabino-hexopyranoside
• CAS: 611210-64-1
• 化学式: C₁₄H₂₉N₃O₄Si
• 分子量: 331.487
• InChiKey: LNQUJHXDQWRBGE-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-tert-butyldimethylsilyloxyethyl 3-azido-2,3,6-trideoxy-β-D-arabino-hexopyranoside 在 Lindlar's catalyst 2,6-二甲基吡啶 、 氢气 、 potassium carbonate 、 氟化氢吡啶 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  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 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.25h， 生成 2-tert-butyldimethylsilyloxyethyl 3-azido-2,3,6-trideoxy-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