6,6'-bis-O-(3-octylundecanoyl)-α,α'-trehalose | 1223421-02-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 6,6'-bis-O-(3-octylundecanoyl)-α,α'-trehalose
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(3-octylundecanoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 3-octylundecanoate
• CAS: 1223421-02-0
• 化学式: C₅₀H₉₄O₁₃
• 分子量: 903.289
• InChiKey: DKYBDKATJDCSMX-KCNGAROKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  63
• 可旋转键数：
  40
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  202
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  6,6'-bis-O-(3-octylundecanoyl)-2,3,4,2',3',4'-hexabenzyl-α,α'-trehalose 在 palladium hydroxide, 20 wt% on carbon 、 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 以75%的产率得到6,6'-bis-O-(3-octylundecanoyl)-α,α'-trehalose
  参考文献：
  名称：

  Development of Vizantin, a Safe Immunostimulant, Based on the Structure–Activity Relationship of Trehalose-6,6′-dicorynomycolate

  摘要：

  Vizantin, 6,6'-bis-O-(3-nonyldodecanoy1)-alpha,alpha'-trehalose, was developed as a safe immunostimulator on the basis of a structure-activity relationship (SAR) study with trehalose 6,6'-dicorynomycolate (TDCM). It was possible to synthesize vizantin on a large scale more easily than in the case of TDCM, and the compound exhibited more potent prophylactic effect on experimental lung metastasis of B16-F0 melanoma cells. Because vizantin stimulated human macrophages, it is a promising candidate for clinical application.

  DOI：

  10.1021/jm3016443

文献信息

• Development of Vizantin, a Safe Immunostimulant, Based on the Structure–Activity Relationship of Trehalose-6,6′-dicorynomycolate
  作者：Hirofumi Yamamoto、Masataka Oda、Mayo Nakano、Naoyuki Watanabe、Kenta Yabiku、Masahiro Shibutani、Masahisa Inoue、Hiroshi Imagawa、Masahiro Nagahama、Seiichiro Himeno、Kojun Setsu、Jun Sakurai、Mugio Nishizawa

  DOI：10.1021/jm3016443

  日期：2013.1.10

  Vizantin, 6,6'-bis-O-(3-nonyldodecanoy1)-alpha,alpha'-trehalose, was developed as a safe immunostimulator on the basis of a structure-activity relationship (SAR) study with trehalose 6,6'-dicorynomycolate (TDCM). It was possible to synthesize vizantin on a large scale more easily than in the case of TDCM, and the compound exhibited more potent prophylactic effect on experimental lung metastasis of B16-F0 melanoma cells. Because vizantin stimulated human macrophages, it is a promising candidate for clinical application.