2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside | 258857-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside
• 英文别名: 2-[(2S,4R,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-4-(dimethylamino)-6-methyloxan-2-yl]oxyethanol
• CAS: 258857-73-7
• 化学式: C₁₆H₃₅NO₄Si
• 分子量: 333.544
• InChiKey: BSRNYQBCLUNEOS-APIJFGDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 生成 2-Phenyl-quinoline-4-carboxylic acid 2-((2S,4R,5S,6R)-4-dimethylamino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethyl ester
  参考文献：
  名称：

  2-Phenylquinoline-Carbohydrate Hybrids: Molecular Design, Chemical Synthesis, and Evaluation of a New Family of Light-Activatable DNA-Cleaving Agents

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19991216)38:24<3733::aid-anie3733>3.0.co;2-w
• 作为产物：
  描述：

  phenyl 3-azido-4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-1-thio-D-arabinohexopyranoside 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 13.0h， 生成 2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside
  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

• 2-Phenylquinoline-Carbohydrate Hybrids: Molecular Design, Chemical Synthesis, and Evaluation of a New Family of Light-Activatable DNA-Cleaving Agents
  作者：Kazunobu Toshima、Ryusuke Takano、Yutaka Maeda、Masataka Suzuki、Akira Asai、Shuichi Matsumura

  DOI：10.1002/(sici)1521-3773(19991216)38:24<3733::aid-anie3733>3.0.co;2-w

  日期：1999.12.16
• 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.