6,6'-bis-O-[(2R,3R)-3-methoxy-2-tetradecyloctadecanoyl]-2,3,4,2',3',4'-hexa-O-benzyl-α,α'-trehalose | 1416474-03-7

• 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-[(2R,3R)-3-methoxy-2-tetradecyloctadecanoyl]-2,3,4,2',3',4'-hexa-O-benzyl-α,α'-trehalose
• 英文别名: [(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[[(2R,3R)-3-methoxy-2-tetradecyloctadecanoyl]oxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl (2R,3R)-3-methoxy-2-tetradecyloctadecanoate
• CAS: 1416474-03-7
• 化学式: C₁₂₀H₁₈₆O₁₅
• 分子量: 1868.79
• InChiKey: QLDWCLNQWPEQOG-QKBHJSTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  38.1
• 重原子数：
  135
• 可旋转键数：
  86
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  6,6'-bis-O-[(2R,3R)-3-methoxy-2-tetradecyloctadecanoyl]-2,3,4,2',3',4'-hexa-O-benzyl-α,α'-trehalose 在 palladium(II) hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 3.0h， 以87%的产率得到6,6'-bis-O-[(2R,3R)-3-methoxy-2-tetradecyloctadecanoyl]-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
• 作为产物：
  描述：

  (2R,3R)-3-methoxy-2-tetradecyloctadecanoic acid 、 [(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到6,6'-bis-O-[(2R,3R)-3-methoxy-2-tetradecyloctadecanoyl]-2,3,4,2',3',4'-hexa-O-benzyl-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.