p-tolyl 2,3-di-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside | 1380233-69-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2,3-di-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside
• 英文别名: p-tolyl 2,3-Di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-4,5-bis[(4-methoxyphenyl)methoxy]-6-(4-methylphenyl)sulfanyloxan-3-ol
• CAS: 1380233-69-1
• 化学式: C₂₉H₃₄O₇S
• 分子量: 526.651
• InChiKey: XLPVAXOFJWWCSR-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-tolyl 2,3-di-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside 在 吡啶 、 吗啉,4-(苯基亚硫酰基)- 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.83h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(4,6-di-O-benzyl-2,3-O-carbonyl-β-D-glucopyranosyl)-(1->6)-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-甲氧基氯苄 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 11.5h， 生成 p-tolyl 2,3-di-O-(4-methoxybenzyl)-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

文献信息

• H₂SO₄-Silica: An Efficient Promoter for Selective Removal of Benzylidene and Isopropylidene Groups in the Presence of<i>p</i>-Methoxybenzyl Group
  作者：Prashant Rajan Verma、Balaram Mukhopadhyay

  DOI：10.1080/07328303.2015.1069829

  日期：2015.7.24

  GRAPHICAL ABSTRACT Selective removal of the benzylidene and isopropylidene protections in the presence of acid-labile p-methoxybenzyl group using H2SO4-silica in methanol is reported. The deprotection reactions were found to be clean and result in the desired products in good to excellent yields.

  报道了在甲醇中使用H 2 SO 4-二氧化硅在酸不稳定的对甲氧基苄基存在下选择性除去亚苄基和异亚丙基保护基的报道。发现脱保护反应是干净的，并以良好至优异的收率得到期望的产物。