methyl 3-chloro-2,3,6-trideoxy-4-O-trifluoromethanesulfonyl-α-L-arabino-hexopyranoside | 184778-24-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: methyl 3-chloro-2,3,6-trideoxy-4-O-trifluoromethanesulfonyl-α-L-arabino-hexopyranoside
• 英文别名: [(2S,3S,4S,6R)-4-chloro-6-methoxy-2-methyloxan-3-yl] trifluoromethanesulfonate
• CAS: 184778-24-3
• 化学式: C₈H₁₂ClF₃O₅S
• 分子量: 312.694
• InChiKey: ZLRPDNFJYFWMKL-YTLHQDLWSA-N

物化性质

• 沸点：
  322.9±42.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-chloro-2,3,6-trideoxy-4-O-trifluoromethanesulfonyl-α-L-arabino-hexopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以74%的产率得到(2S,3R,4S,6R)-3-Azido-4-chloro-6-methoxy-2-methyl-tetrahydro-pyran
  参考文献：
  名称：

  Synthesis and biological activity of 4′-azido- and 4′-trifluoracetamido-3′-chloro-3′-deamino-4′-deoxydaunorubicin

  摘要：

  The syntheses of 1-O-acetyl-4-azido-3-chloro-L-lyxo-hexopyranose and 1-O-acetyl-3-chloro-4-trifluoracetamido-L-lyxo-hexopyranose are described. These aminosugars were successfully employed for the synthesis of 4'-azido-3'-chloro-3'-deamino-4'-deoxydaunorubicin and 3'-chloro-3'-deamino-4'-deoxy-4'-trifluoracetamidodaunorubicin. The cytotoxicity of the above-mentioned compounds is discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00457-x
• 作为产物：
  描述：

  三氟甲磺酸酐 、 methyl-4-O-acetyl-3-chloro-2,3,6-trideoxy-α-L-arabino-hexopyranoside 在 4-二甲氨基吡啶 、 sodium methylate 作用下， 生成 methyl 3-chloro-2,3,6-trideoxy-4-O-trifluoromethanesulfonyl-α-L-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis and biological activity of 4′-azido- and 4′-trifluoracetamido-3′-chloro-3′-deamino-4′-deoxydaunorubicin

  摘要：

  The syntheses of 1-O-acetyl-4-azido-3-chloro-L-lyxo-hexopyranose and 1-O-acetyl-3-chloro-4-trifluoracetamido-L-lyxo-hexopyranose are described. These aminosugars were successfully employed for the synthesis of 4'-azido-3'-chloro-3'-deamino-4'-deoxydaunorubicin and 3'-chloro-3'-deamino-4'-deoxy-4'-trifluoracetamidodaunorubicin. The cytotoxicity of the above-mentioned compounds is discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00457-x

文献信息

• Design, Synthesis and Biological Activity of 7-O-(4-O-Acetyl-3-iodo-2,3,6-trideoxy-.ALPHA.-L-arabino-hexopyranosyl)daunomycinone and 7-O-(3-Chloro-2,3,6-trideoxy-4-O-propanoyl-.ALPHA.-L-lyxo-hexopyranosyl)daunomycinone.
  作者：Nectarios ALIGIANNIS、Nicole POULI、Panagiotis MARAKOS、Sofia MITAKU、Alexios-Leandros SKALTSOUNIS、Stephane LEONCE、Alain PIERRE、Ghanem ATASSI

  DOI：10.1248/cpb.48.150

  日期：——

  The synthesis and pharmacological evaluation of 7-O-(4-O-acetyl-3-iodo-2, 3, 6-trideoxy-α-L-arabino-hexopy-ranosyl)daunomycinone and 7-O-(3-chloro-2, 3, 6-trideoxy-4-O-propanoyl-α-L-lyxo-hexopyranosyl)daunomycinone are described. Their cytotoxic activity was evaluated against normal and resistant cell lines. Both compounds exhibited activity against the adriamycin resistant cell line KB-A1. These results support the hypothesis that the increased lipophilicity of the sugar part of anthracyclines is associated with their ability to overcome multidrug resistance (MDR).

  本文描述了 7-O-(4-O-乙酰基-3-碘-2, 3, 6-三脱氧-α-L-阿拉伯并六吡喃糖基)大诺霉素酮和 7-O-(3-氯-2, 3, 6-三脱氧-4-O-丙酰-α-L-来苏己吡喃糖基)大诺霉素酮的合成和药理学评价。评估了它们对正常细胞系和耐药细胞系的细胞毒活性。这两种化合物对阿霉素耐药细胞株 KB-A1 均有活性。这些结果支持了这样的假设，即蒽环类药物中糖部分的亲脂性增加与其克服多药耐药性（MDR）的能力有关。
• Synthesis and biological activity of 4′-azido- and 4′-trifluoracetamido-3′-chloro-3′-deamino-4′-deoxydaunorubicin
  作者：Nectarios Aligiannis、Nicole Pouli、Panagiotis Marakos、Alexios-Leandros Skaltsounis、Stephane Leonce、Alain Pierre、Ghanem Atassi

  DOI：10.1016/0960-894x(96)00457-x

  日期：1996.10

  The syntheses of 1-O-acetyl-4-azido-3-chloro-L-lyxo-hexopyranose and 1-O-acetyl-3-chloro-4-trifluoracetamido-L-lyxo-hexopyranose are described. These aminosugars were successfully employed for the synthesis of 4'-azido-3'-chloro-3'-deamino-4'-deoxydaunorubicin and 3'-chloro-3'-deamino-4'-deoxy-4'-trifluoracetamidodaunorubicin. The cytotoxicity of the above-mentioned compounds is discussed. Copyright (C) 1996 Elsevier Science Ltd