2-tert-butyldimethylsilyloxyethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-D-arabino-hexopyranoside | 611210-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-tert-butyldimethylsilyloxyethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-D-arabino-hexopyranoside
• 英文别名: N-[(2R,3S,4R,6S)-3-[tert-butyl(dimethyl)silyl]oxy-6-[2-[tert-butyl(dimethyl)silyl]oxyethoxy]-2-methyloxan-4-yl]-4-nitrobenzenesulfonamide
• CAS: 611210-59-4
• 化学式: C₂₆H₄₈N₂O₈SSi₂
• 分子量: 604.913
• InChiKey: ZZHYNVJABSHTDX-OUJCMCIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-tert-butyldimethylsilyloxyethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-D-arabino-hexopyranoside 在 potassium carbonate 、 氟化氢吡啶 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1,4-bis((2-hydroxyethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-D-arabino-hexopyranosid-3-yl)methyl)benzene
  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 Lindlar's catalyst 咪唑 、 2,6-二甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 三氟化硼乙醚 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 35.25h， 生成 2-tert-butyldimethylsilyloxyethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-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

文献信息

• Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents
  作者：Kazunobu Toshima、Tomonori Kimura、Ryusuke Takano、Tomohiro Ozawa、Akiko Ariga、Yutaka Shima、Kazuo Umezawa、Shuichi Matsumura

  DOI：10.1016/s0040-4020(03)00820-2

  日期：2003.8

  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.