methyl (2E,4R,5R,6S,7E)-9-oxo-4,5,6-tris(phenylmethoxy)nona-2,7-dienoate | 215303-14-3

• 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: methyl (2E,4R,5R,6S,7E)-9-oxo-4,5,6-tris(phenylmethoxy)nona-2,7-dienoate
• CAS: 215303-14-3
• 化学式: C₃₁H₃₂O₆
• 分子量: 500.591
• InChiKey: XAEVKVISSBROQP-QXOBEQSCSA-N

物化性质

• 沸点：
  635.665±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.155±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2E,4R,5R,6S,7E)-9-oxo-4,5,6-tris(phenylmethoxy)nona-2,7-dienoate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium chlorite 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate 、 D-(-)-酒石酸二乙酯 、 4 A molecular sieve 、 双氧水 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 异辛烷 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 35.34h， 生成 (2S,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

  摘要：

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.

  DOI：

  10.1021/jo981211d
• 作为产物：
  描述：

  D-xylose diethyl dithioacetal 在 咪唑 、 四丙基高钌酸铵 、 4 A molecular sieve 、 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 、 N-甲基吗啉氧化物 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 38.33h， 生成 methyl (2E,4R,5R,6S,7E)-9-oxo-4,5,6-tris(phenylmethoxy)nona-2,7-dienoate
  参考文献：
  名称：

  Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

  摘要：

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.

  DOI：

  10.1021/jo981211d

文献信息

• Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol
  作者：Frederick E. Ziegler、Yizhe Wang

  DOI：10.1021/jo981211d

  日期：1998.10.1

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.