1,2,3,6-tetra-O-acetyl-4-O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-α,β-D-glucopyranose | 75795-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,6-tetra-O-acetyl-4-O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-α,β-D-glucopyranose
• 英文别名: 1,2,3,6-tetra-O-acetyl-4-O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose
• CAS: 75795-61-8；75795-68-5
• 化学式: C₂₄H₃₄O₁₇
• 分子量: 594.524
• InChiKey: BHNGDVMMXNUCOL-XZYTYGINSA-N

物化性质

• 沸点：
  659.0±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.97
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  225.95
• 氢给体数：
  2.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-α,β-D-glucopyranose 在 palladium on activated charcoal 四乙基溴化铵 、 氢气 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 104.5h， 生成 3'-岩藻糖基乳糖
  参考文献：
  名称：

  O-αl-呋喃果糖基-（1→3）-O-β-d-吡喃半乳糖基-（1→4）-d-葡萄糖（3'-O-α-l-呋喃果糖基乳糖）的合成及改进的合成路线其β-（1″→3′）-连接的异构体

  摘要：

  摘要乳糖与2,2-二甲氧基丙烷在N，N-二甲基-甲酰胺中于80-85°进行异丙基异丙基化反应，得到动力学上有利的4'，6'-乙缩醛1和热力学上更稳定的3'的1：2混合物， 4'-乙缩醛2，通过色谱法分离。1,2,3,6,2'，6'-六乙酸酯（3）和1,2,3,6,2'，6'-六苯甲酸酯（4）以及相应的脱丙酮酯图5和图6是通过标准程序制备的。1,2,3,6,2'，6'-六-O-乙酰基-α，β-乳糖（5）与2,3,4三-O-苯甲酰基-1-呋喃核糖基溴的缩合反应溴离子催化得到α-（1''→3'）-连接的被保护的三糖8。脱乙酰基，然后氢解除去苄基，得到标题三糖10。六乙酸酯5也与2,3,4-三-O-乙酰基-α-1-呋喃核糖基溴化物缩合，

  DOI：

  10.1016/s0008-6215(00)85429-4
• 作为产物：
  描述：

  在 甲醇 作用下， 反应 4.5h， 以92%的产率得到1,2,3,6-tetra-O-acetyl-4-O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-α,β-D-glucopyranose
  参考文献：
  名称：

  Integrating ReSET with Glycosyl Iodide Glycosylation in Step-Economy Syntheses of Tumor-Associated Carbohydrate Antigens and Immunogenic Glycolipids

  摘要：

  Carbohydrates mediate a wide range of biological processes, and understanding these events and how they might be influenced is a complex undertaking that requires access to pure glycoconjugates. The isolation of sufficient quantities of carbohydrates and glycolipids from biological samples remains a significant challenge that has redirected efforts toward chemical synthesis. However, progress toward complex glycoconjugate total synthesis has been slowed by the need for multiple protection and deprotection steps owing to the large number of similarly reactive hydroxyls in carbohydrates. Two methodologies, regioselective silyl exchange technology (ReSET) and glycosyl iodide glycosylation have now been integrated to streamline the synthesis of the globo series trisaccharides (globotriaose and isoglobotriaose) and alpha-lactosylceramide (alpha-LacCer). These glycoconjugates include tumor-associated carbohydrate antigens (TACAs) and immunostimulatory glycolipids that hold promise as immunotherapeutics. Beyond the utility of the step-economy syntheses afforded by this synthetic platform, the studies also reveal a unique electronic interplay between acetate and silyl ether protecting groups. Incorporation of acetates proximal to silyl ethers attenuates their reactivity while reducing undesirable side reactions. This phenomenon can be used to fine-tune the reactivity of silylated/acetylated sugar building blocks.

  DOI：

  10.1021/jo402736g