((2R,3S,4S,5R,6S)-3-acetoxy-4,5-bis((4-methoxybenzyl)oxy)-6-(p-tolylthio)tetrahydro-2H-pyran-2-yl)methyl acetate | 1394826-64-2

• 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,6S)-3-acetoxy-4,5-bis((4-methoxybenzyl)oxy)-6-(p-tolylthio)tetrahydro-2H-pyran-2-yl)methyl acetate
• CAS: 1394826-64-2
• 化学式: C₃₃H₃₈O₉S
• 分子量: 610.725
• InChiKey: WNXFPKGBGVNFCT-CYEGLCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  43.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ((2R,3S,4S,5R,6S)-3-acetoxy-4,5-bis((4-methoxybenzyl)oxy)-6-(p-tolylthio)tetrahydro-2H-pyran-2-yl)methyl acetate 在 吡啶 、 二苯基亚砜 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl (4,6-di-O-acetyl-2,3-O-carbonyl-α-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Lewis Acids as α-Directing Additives in Glycosylations by Using 2,3-O-Carbonate-Protected Glucose and Galactose Thioglycoside Donors Based on Preactivation Protocol

  摘要：

  Catalytic or stoichiometric amounts of Lewis acids were found to be very effective a-directing additives in the stereoselective glycosylations of diverse 2,3-O-carbonate-protected glucose and galactose thioglycoside donors by preactivation protocol. The poor stereoselectivities of 4,6-di-O-acetyl-2,3-O-carbonate protected thioglycoside donors in glycosyl coupling reactions were greatly improved, and excellent alpha-stereoselectivities were achieved by the addition of 0.2 equiv of BF3 center dot OEt2. On the other hand, the beta-selectivities of 4,6-di-O-benzyl-2,3-O-carbonate-protected thioglucoside donor toward glycosylations were reversed completely to the alpha-selectivities by the use of 1 equiv of SnCl4, making the stereoselectivity controllable. Furthermore, the poor stereoselectivities of 4,6-di-O-benzyl-2,3-O-carbonate-protected thiogalactoside donor in glycosylations were also improved by using SnCl4 as additive.

  DOI：

  10.1021/jo3002084
• 作为产物：
  描述：

  4-methylphenyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 ((2R,3S,4S,5R,6S)-3-acetoxy-4,5-bis((4-methoxybenzyl)oxy)-6-(p-tolylthio)tetrahydro-2H-pyran-2-yl)methyl acetate
  参考文献：
  名称：

  Lewis Acids as α-Directing Additives in Glycosylations by Using 2,3-O-Carbonate-Protected Glucose and Galactose Thioglycoside Donors Based on Preactivation Protocol

  摘要：

  Catalytic or stoichiometric amounts of Lewis acids were found to be very effective a-directing additives in the stereoselective glycosylations of diverse 2,3-O-carbonate-protected glucose and galactose thioglycoside donors by preactivation protocol. The poor stereoselectivities of 4,6-di-O-acetyl-2,3-O-carbonate protected thioglycoside donors in glycosyl coupling reactions were greatly improved, and excellent alpha-stereoselectivities were achieved by the addition of 0.2 equiv of BF3 center dot OEt2. On the other hand, the beta-selectivities of 4,6-di-O-benzyl-2,3-O-carbonate-protected thioglucoside donor toward glycosylations were reversed completely to the alpha-selectivities by the use of 1 equiv of SnCl4, making the stereoselectivity controllable. Furthermore, the poor stereoselectivities of 4,6-di-O-benzyl-2,3-O-carbonate-protected thiogalactoside donor in glycosylations were also improved by using SnCl4 as additive.

  DOI：

  10.1021/jo3002084