[(2R,3S,4R)-6-acetyloxy-4-(dimethylamino)-2-methyloxan-3-yl] benzoate | 309722-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R)-6-acetyloxy-4-(dimethylamino)-2-methyloxan-3-yl] benzoate
• CAS: 309722-45-0
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: JGWXEJNDHYIMGS-XKAGKQMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R)-6-acetyloxy-4-(dimethylamino)-2-methyloxan-3-yl] benzoate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2R,3S,4R,6S)-6-[2-(9H-β-Carbolin-1-yl)-ethoxy]-4-dimethylamino-2-methyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  β-Carboline–Carbohydrate hybrids: molecular design, chemical synthesis and evaluation of novel DNA photocleavers

  摘要：

  beta-Carboline present in beta-carboline alkaloids from marine organisms was found, for the first time, to cleave DNA at the guanine site upon irradiation with UV light with a long wavelength without any additive, and beta-carboline-carbohydrate hybrid system was effective for DNA cleavage. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00828-9

文献信息

• Carbohydrate-modulated DNA photocleavage: design, synthesis, and evaluation of novel glycosyl anthraquinones
  作者：Kazunobu Toshima、Yutaka Maeda、Hiromi Ouchi、Akira Asai、Shuichi Matsumura

  DOI：10.1016/s0960-894x(00)00410-8

  日期：2000.10

  Novel and artificial anthraquinone-carbohydrate hybrids were designed and synthesized, and found to effectively cleave DNA under irradiation with a long wavelength UV light and also exhibit cytotoxicity against HeLa S3 cells.

  设计并合成了新型和人工合成的蒽醌-碳水化合物杂化物，发现在长波长紫外线照射下可有效切割DNA，并且还表现出对HeLa S3细胞的细胞毒性。
• Molecular design, chemical synthesis, and evaluation of cytosine–carbohydrate hybrids for selective recognition of a single guanine bulged duplex DNA
  作者：Yusuke Idutsu、Ayaka Sasaki、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1016/j.bmcl.2005.06.073

  日期：2005.10

  The designed cytosine-carbohydrate hybrid molecule selectively recognized and stabilized the bulged duplex DNA possessing the complementary bulged DNA base, guanine, while the nucleotide base itself did not exhibit any such ability. It was also found that the assistance of the carbohydrate to stabilize the interaction between the nucleotide base and the complementally bulge DNA base is very helpful for the selective recognition and stabilization of the single-bulged duplex DNA. (c) 2005 Elsevier Ltd. All rights reserved.
• Efficient C-arylglycosylation of 1-O-methyl sugar by novel use of TMSOTf-AgClO4 catalyst system
  作者：Kazunobu Toshima、Goh Matsuo、Kuniaki Tatsuta

  DOI：10.1016/0040-4039(92)88170-a

  日期：1992.4

  Highly beta-stereoselective C-arylglycosylations of the 1-O-methyl sugars 1 approximately 4 with 2-naphthol (9) were effectively achieved by novel combinational use of a catalytic amount of TMSOTf-AgClO4 as an activator. Also, C-arylglycosylations of the 1-O-acetyl sugars 5 approximately 8 with 9 in this way worked as well.