(2S)-2-O-(p-methoxybenzyl)-3-O-(p-toluenesulfonyl)-1-O-vinylglycerol | 301298-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-O-(p-methoxybenzyl)-3-O-(p-toluenesulfonyl)-1-O-vinylglycerol
• 英文别名: [(2S)-3-ethenoxy-2-[(4-methoxyphenyl)methoxy]propyl] 4-methylbenzenesulfonate
• CAS: 301298-60-2
• 化学式: C₂₀H₂₄O₆S
• 分子量: 392.473
• InChiKey: SFTFBUDVSBUFDQ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  氯磺酰异氰酸酯 、 (2S)-2-O-(p-methoxybenzyl)-3-O-(p-toluenesulfonyl)-1-O-vinylglycerol 在 sodium carbonate 、 红铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (2R,4'R)-2-O-(azetidin-2'-onyl-4')-2-O-(p-methoxybenzyl)-3-O-(p-toluenesulfonyl)glycerol 、 (2R,4'S)-2-O-(azetidin-2'-onyl-4')-2-O-(p-methoxybenzyl)-3-O-(p-toluenesulfonyl)glycerol
  参考文献：
  名称：

  Strategies for the Formation of 1-Dethia-1-oxa-cephams

  摘要：

  The paper describes three possible routes for the formation of 1-dethia-1-oxa-cephams. The first two routes: (a) [2+2]cycloaddition to chiral vinyl ethers and (b) condensation of 4-acetoxyazetidin-2-one to chiral alcohols, are followed by the ring closure step involving N-alkylation. The third route (c) consists of N-alkylation prior to the cyclization step. In order to compare routes (a), (b) and (c), diastereomeric 1-dethia-3-(4-methoxybenzyloxy)-1-oxacephams were synthesized using three possible strategies. While the comparison of stereoselectivities of the [2+2]cycloaddition method (a) and the condensation (b) shows unequivocally the advantage of the former, the route (c) leads to the reverse direction of asymmetric induction relative to the first two steps and offers the highest asymmetric induction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00405-1
• 作为产物：
  描述：

  2,5-di-O-(4-methoxybenzyl)-D-mannitol 在 吡啶 、 sodium periodate 、 三氟甲磺酸三甲基硅酯 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 53.17h， 生成 (2S)-2-O-(p-methoxybenzyl)-3-O-(p-toluenesulfonyl)-1-O-vinylglycerol
  参考文献：
  名称：

  Strategies for the Formation of 1-Dethia-1-oxa-cephams

  摘要：

  The paper describes three possible routes for the formation of 1-dethia-1-oxa-cephams. The first two routes: (a) [2+2]cycloaddition to chiral vinyl ethers and (b) condensation of 4-acetoxyazetidin-2-one to chiral alcohols, are followed by the ring closure step involving N-alkylation. The third route (c) consists of N-alkylation prior to the cyclization step. In order to compare routes (a), (b) and (c), diastereomeric 1-dethia-3-(4-methoxybenzyloxy)-1-oxacephams were synthesized using three possible strategies. While the comparison of stereoselectivities of the [2+2]cycloaddition method (a) and the condensation (b) shows unequivocally the advantage of the former, the route (c) leads to the reverse direction of asymmetric induction relative to the first two steps and offers the highest asymmetric induction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00405-1

文献信息

• Strategies for the Formation of 1-Dethia-1-oxa-cephams
  作者：Z Kałuża、B Furman、P Krajewski、M Chmielewski

  DOI：10.1016/s0040-4020(00)00405-1

  日期：2000.7

  The paper describes three possible routes for the formation of 1-dethia-1-oxa-cephams. The first two routes: (a) [2+2]cycloaddition to chiral vinyl ethers and (b) condensation of 4-acetoxyazetidin-2-one to chiral alcohols, are followed by the ring closure step involving N-alkylation. The third route (c) consists of N-alkylation prior to the cyclization step. In order to compare routes (a), (b) and (c), diastereomeric 1-dethia-3-(4-methoxybenzyloxy)-1-oxacephams were synthesized using three possible strategies. While the comparison of stereoselectivities of the [2+2]cycloaddition method (a) and the condensation (b) shows unequivocally the advantage of the former, the route (c) leads to the reverse direction of asymmetric induction relative to the first two steps and offers the highest asymmetric induction. (C) 2000 Elsevier Science Ltd. All rights reserved.