p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(2,4,6-trimethoxybenzyl)amino]-1-thio-β-D-glucopyranoside | 1276031-24-3

• 分子结构分类: 有机化合物
• 英文名称: p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(2,4,6-trimethoxybenzyl)amino]-1-thio-β-D-glucopyranoside
• CAS: 1276031-24-3
• 化学式: C₃₁H₃₉NO₁₁S
• 分子量: 633.717
• InChiKey: QLHURNWNXMXZSR-CWMPKMHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  136.13
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(2,4,6-trimethoxybenzyl)amino]-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 2,4,6-三叔丁基吡啶 、 三氟甲磺酸三甲基硅酯 、 氨 、 sodium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 乙基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Comparing the use of 2-methylenenapthyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl and 2,4,6-trimethoxybenzyl as N–H protecting groups for p-tolyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-d-glucosides

  摘要：

  A hurdle in glycosylation reactions of 2-acetamido glycosyl donors is the formation of a stable and unreactive oxazoline that decreases the yield of these reactions significantly. As an effort to prevent oxazoline formation during glycosylation reactions, we protected the N-H of the acetamido group within a 2-acetamido-2-deoxy-1-thio-beta-D-glucoside with one of four different protecting groups. These groups were either 2-methylenenapthyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl or 2,4,6-trimethoxybenzyl. The resulting N-alkylacetamides were then used in glycosylation reactions with ethanol as a model acceptor. We observed that the ethyl glycosides obtained in each case were obtained with exclusive 3-selectivity without the formation of oxazoline sideproducts. The resulting products were then used to screen conditions for protecting group removal. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.026
• 作为产物：
  描述：

  p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 三乙酰氧基硼 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 38.0h， 生成 p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(2,4,6-trimethoxybenzyl)amino]-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Comparing the use of 2-methylenenapthyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl and 2,4,6-trimethoxybenzyl as N–H protecting groups for p-tolyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-d-glucosides

  摘要：

  A hurdle in glycosylation reactions of 2-acetamido glycosyl donors is the formation of a stable and unreactive oxazoline that decreases the yield of these reactions significantly. As an effort to prevent oxazoline formation during glycosylation reactions, we protected the N-H of the acetamido group within a 2-acetamido-2-deoxy-1-thio-beta-D-glucoside with one of four different protecting groups. These groups were either 2-methylenenapthyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl or 2,4,6-trimethoxybenzyl. The resulting N-alkylacetamides were then used in glycosylation reactions with ethanol as a model acceptor. We observed that the ethyl glycosides obtained in each case were obtained with exclusive 3-selectivity without the formation of oxazoline sideproducts. The resulting products were then used to screen conditions for protecting group removal. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.026