(2S,3R,4S,6S)-2-(2-(benzyloxy)ethyl)-6-(hydroxymethyl)-3-methyltetrahydro-2H-pyran-4-ol | 1350818-12-0

• 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,3R,4S,6S)-2-(2-(benzyloxy)ethyl)-6-(hydroxymethyl)-3-methyltetrahydro-2H-pyran-4-ol
• 英文别名: (2S,3R,4S,6S)-6-(hydroxymethyl)-3-methyl-2-(2-phenylmethoxyethyl)oxan-4-ol
• CAS: 1350818-12-0
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: QBMZTZUPFGCFQN-OEAJRASXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,6S)-2-(2-(benzyloxy)ethyl)-6-(hydroxymethyl)-3-methyltetrahydro-2H-pyran-4-ol 在 甲醇 、 乙醚 、 potassium tert-butylate 、 对甲苯磺酸 、 臭氧 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 45.5h， 生成
  参考文献：
  名称：

  Total synthesis of cryptophycin-24 (arenastatin A) via Prins cyclization

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.09.134
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (2S,3R,4S,6S)-2-(2-(benzyloxy)ethyl)-6-(hydroxymethyl)-3-methyltetrahydro-2H-pyran-4-ol
  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

• Synthesis of spiroketal fragment of ossamycin via Prins cyclization
  作者：J.S. Yadav、Md. Ataur Rahman、N. Mallikarjuna Reddy、A.R. Prasad

  DOI：10.1016/j.tetlet.2014.11.097

  日期：2015.1

  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.
• 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.