(2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran | 107855-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran
• 英文别名: benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-glucopyranoside
• CAS: 107855-18-5
• 化学式: C₆₈H₇₀O₁₁
• 分子量: 1063.3
• InChiKey: FAJQIEXBXPLLGC-PFAFENKSSA-N

物化性质

• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  79.0
• 可旋转键数：
  28.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101.53
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  苄基2,3,6-三-O-苄基吡喃己糖苷 、 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl fluoride 在 四氟化钛 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以36%的产率得到(2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Glycosylation employing glycopyranosyl fluorides promoted by TiF₄ under mild conditions

  摘要：

  Glycopyranosyl fluorides are shown as efficient glycosyl donors by glycosylation of appropriate aglycon structures under mild conditions with Lewis acid catalysis in anhydrous ether or acetonitrile. Further direct reaction sequences gave naturally occurring disaccharide derivatives of biological interest.

  DOI：

  10.1080/07328303.2020.1837151

文献信息

• A rapid and efficient synthesis of 1,2-trans-β-linked glycosides via benzyl- or benzoyl-protected glycopyranosyl phosphates
  作者：Shun-ichi Hashimoto、Takeshi Honda、Shiro Ikegami

  DOI：10.1039/c39890000685

  日期：——

  A highly stereocontrolled construction of 1,2-trans-β-glycosidic linkage with or without neighbouring-group participation has been achieved using benzyl- or benzoyl-protected glycopyranosyl phosphates as glycosyl donors in the presence of trimethylsilyl triflate (TMSOTf).

  在存在三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）的情况下，使用苄基或苯甲酰基保护的吡喃葡萄糖基磷酸酯作为糖基供体，已经实现了具有或不具有邻基参与的1,2-反式-β-糖苷键的高度立体控制的构建。
• An extremely mild and general method for the stereocontrolled construction of 1,2-cis-glycosidic linkages via S-glycopyranosyl phosphorodiamidimidothioates
  作者：Hashimoto Shun-ichi、Honda Takeshi、Ikegami Shiro

  DOI：10.1016/s0040-4039(00)97729-3

  日期：——
• An efficient approach to O-glycosides through CuBr2-Bu4NBr mediated activation of glycosides
  作者：Susumu Sato、Masato Mori、Yukishige Ito、tomoya Ogawa

  DOI：10.1016/s0008-6215(00)90163-0

  日期：1986.11