1,3-di-O-hexanoyl-2-O-β-D-glucopyranosyl-glycerol | 1190208-49-1

• 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-β-D-glucopyranosyl-glycerol
• 英文别名: [3-hexanoyloxy-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] hexanoate
• CAS: 1190208-49-1
• 化学式: C₂₁H₃₈O₁₀
• 分子量: 450.527
• InChiKey: FFPCAZMUDTXKSB-CMWLGVBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,3-di-O-hexanoyl-2-O-(2,3,4,6-tetra-O-chloroacetyl-β-D-glucopyranosyl)-glycerol 在 乙酸肼 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 18.0h， 以60%的产率得到1,3-di-O-hexanoyl-2-O-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

文献信息

• 2-O-β-d-Glucopyranosyl-sn-glycerol based analogues of sulfoquinovosyldiacylglycerols (SQDG) and their role in inhibiting Epstein-Barr virus early antigen activation
  作者：Milind Dangate、Laura Franchini、Fiamma Ronchetti、Takanari Arai、Akira Iida、Harukuni Tokuda、Diego Colombo

  DOI：10.1016/j.bmc.2009.06.064

  日期：2009.8

  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.