[(2R,3S,4R)-2-(hydroxymethyl)-3-phenylmethoxy-3,4-dihydro-2H-pyran-4-yl] benzoate | 120927-56-2

• 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: [(2R,3S,4R)-2-(hydroxymethyl)-3-phenylmethoxy-3,4-dihydro-2H-pyran-4-yl] benzoate
• CAS: 120927-56-2
• 化学式: C₂₀H₂₀O₅
• 分子量: 340.376
• InChiKey: PWHQDKNEWHHTEB-QRVBRYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R)-2-(hydroxymethyl)-3-phenylmethoxy-3,4-dihydro-2H-pyran-4-yl] benzoate 在 4 A molecular sieve 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 Ethyl 3-O-Benzoyl-4-O-benzyl-1,3,6,7-tetradeoxy-D-arabino-octa-1,6(E)-dieno-1,5-pyranose Uronate
  参考文献：
  名称：

  Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes

  摘要：

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.

  DOI：

  10.1021/jo00028a033

文献信息

• Intramolecular radical cyclizations of 2-deoxy-2-iodohexopyranoside derivatives: routes to densely functionalized carbocycles
  作者：Gregory D. Vite、Ricardo Alonso、Bert Fraser-Reid

  DOI：10.1021/jo00271a005

  日期：1989.5