1,3-di-O-octadecanoyl-2-O-(6-deoxy-6-thioacetyl-β-D-glucopyranosyl)-glycerol | 1190208-53-7

• 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-octadecanoyl-2-O-(6-deoxy-6-thioacetyl-β-D-glucopyranosyl)-glycerol
• CAS: 1190208-53-7
• 化学式: C₄₇H₈₈O₁₀S
• 分子量: 845.276
• InChiKey: UHVKPUHGRTZUOQ-FOKSGGAVSA-N

反应信息

• 作为反应物：
  描述：

  1,3-di-O-octadecanoyl-2-O-(6-deoxy-6-thioacetyl-β-D-glucopyranosyl)-glycerol 在 oxone 、 potassium acetate 、 溶剂黄146 、 sodium chloride 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 6.0h， 以40%的产率得到1,3-di-O-octadecanoyl-2-O-β-D-sulfoquinovopyranosyl-glycerol sodium salt
  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-octadecanoyl-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70%的产率得到1,3-di-O-octadecanoyl-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