(2E,7E)-(4R,5R,6S)-4,5,6-Tris-benzyloxy-9-hydroxy-nona-2,7-dienoic acid methyl ester | 215303-15-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,7E)-(4R,5R,6S)-4,5,6-Tris-benzyloxy-9-hydroxy-nona-2,7-dienoic acid methyl ester
• 英文别名: methyl (2E,4R,5R,6S,7E)-9-hydroxy-4,5,6-tris(phenylmethoxy)nona-2,7-dienoate
• CAS: 215303-15-4
• 化学式: C₃₁H₃₄O₆
• 分子量: 502.607
• InChiKey: GOCUPSSTSOHFSG-QXOBEQSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E,7E)-(4R,5R,6S)-4,5,6-Tris-benzyloxy-9-hydroxy-nona-2,7-dienoic acid methyl ester 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二乙酯 、 4 A molecular sieve 、 戴斯-马丁氧化剂 作用下， 以 异辛烷 、 二氯甲烷 为溶剂， 反应 30.67h， 生成 (E)-(4R,5S,6R)-4,5,6-Tris-benzyloxy-6-((2R,3S)-3-formyl-oxiranyl)-hex-2-enoic 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 、 sodium tetrahydroborate 、 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 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 39.0h， 生成 (2E,7E)-(4R,5R,6S)-4,5,6-Tris-benzyloxy-9-hydroxy-nona-2,7-dienoic 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

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.