p-tolyl 4,6-O-benzylidene-2,3-O-carbonyl-1-thio-β-D-glucopyranoside | 1380233-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: p-tolyl 4,6-O-benzylidene-2,3-O-carbonyl-1-thio-β-D-glucopyranoside
• 英文别名: (1R,2S,6R,7S,9R,12R)-7-(4-methylphenyl)sulfanyl-12-phenyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-4-one
• CAS: 1380233-67-9
• 化学式: C₂₁H₂₀O₆S
• 分子量: 400.452
• InChiKey: ZRXVUOLGVVYTLY-FFDFYAMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  三光气 、 4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以81%的产率得到p-tolyl 4,6-O-benzylidene-2,3-O-carbonyl-1-thio-β-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