((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate | 1350818-14-2

• 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,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate
• CAS: 1350818-14-2
• 化学式: C₂₃H₃₀O₆S
• 分子量: 434.554
• InChiKey: IYPYNVRFVNUALJ-VLSUOOLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate 在 对甲苯磺酸 、 sodium iodide 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 29.0h， 生成 (4S,5R,6S)-4-allyl-6-(2-(benzyloxy)ethyl)-2,2,5-trimethyl-1,3-dioxane
  参考文献：
  名称：

  Synthesis of spiroketal fragment of ossamycin via Prins cyclization

  摘要：

  An asymmetric synthesis of spiroketal fragment of an antitumour antibiotic, ossamycin is described. Coupling of aldehyde and alkyne fragments followed by spiroketalization has afforded the spiroketal sub unit of ossamycin. Both the sub targets were constructed via Prins cyclization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.097
• 作为产物：
  描述：

  3-苄氧基丙醛 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 ((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis of spiroketal fragment of ossamycin via Prins cyclization

  摘要：

  An asymmetric synthesis of spiroketal fragment of an antitumour antibiotic, ossamycin is described. Coupling of aldehyde and alkyne fragments followed by spiroketalization has afforded the spiroketal sub unit of ossamycin. Both the sub targets were constructed via Prins cyclization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.097

文献信息

• Total synthesis of cryptophycin-24 (arenastatin A) via Prins cyclization
  作者：J.S. Yadav、K.V. Purnima、B.V. Subba Reddy、K. Nagaiah、A.K. Ghamdi

  DOI：10.1016/j.tetlet.2011.09.134

  日期：2011.12

  A stereoselective synthesis of fragment A of cryptophycin is achieved utilizing the versatile Prins cyclization. Subsequently, the total synthesis of cryptophycin-24 (arenastatin A) has been accomplished by coupling it with the depsipeptide subunit. (C) 2011 Elsevier Ltd. All rights reserved.