1,3-di-O-hexanoyl-2-O-(6-O-tosyl-β-D-glucopyranosyl)-glycerol | 1190208-52-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,3-di-O-hexanoyl-2-O-(6-O-tosyl-β-D-glucopyranosyl)-glycerol
• CAS: 1190208-52-6
• 化学式: C₂₈H₄₄O₁₂S
• 分子量: 604.716
• InChiKey: IDFJDTAVHSBCCP-FSKOWZIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  41.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  175.12
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,3-di-O-hexanoyl-2-O-(6-O-tosyl-β-D-glucopyranosyl)-glycerol 、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以69%的产率得到1,3-di-O-hexanoyl-2-O-(6-deoxy-6-thioacetyl-β-D-glucopyranosyl)-glycerol
  参考文献：
  名称：

  2-O-β-d-Glucopyranosyl-sn-glycerol based analogues of sulfoquinovosyldiacylglycerols (SQDG) and their role in inhibiting Epstein-Barr virus early antigen activation

  摘要：

  New sulfoquinovosyldiacylglycerols derived from 2-O-beta-D-glucopyranosyl-sn-glycerol, carrying acyl chains of various length on the glycerol moiety, were prepared through a convenient synthetic procedure in which a sulfonate is introduced at the C-6 position of glucose by oxidation of a thioacetate in the presence of the unprotected secondary hydroxyl groups, and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. Our study has allowed to ascertain the role of the 6'-sulfonate group and the need of a free hydroxyl group on the glycerol moiety in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.064
• 作为产物：
  描述：

  1,3-di-O-hexanoyl-2-O-β-D-glucopyranosyl-glycerol 、 对甲苯磺酰氯 在 吡啶 、 zinc dibromide 作用下， 反应 2.0h， 以72%的产率得到1,3-di-O-hexanoyl-2-O-(6-O-tosyl-β-D-glucopyranosyl)-glycerol
  参考文献：
  名称：

  2-O-β-d-Glucopyranosyl-sn-glycerol based analogues of sulfoquinovosyldiacylglycerols (SQDG) and their role in inhibiting Epstein-Barr virus early antigen activation

  摘要：

  New sulfoquinovosyldiacylglycerols derived from 2-O-beta-D-glucopyranosyl-sn-glycerol, carrying acyl chains of various length on the glycerol moiety, were prepared through a convenient synthetic procedure in which a sulfonate is introduced at the C-6 position of glucose by oxidation of a thioacetate in the presence of the unprotected secondary hydroxyl groups, and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. Our study has allowed to ascertain the role of the 6'-sulfonate group and the need of a free hydroxyl group on the glycerol moiety in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.064