(2R,3S)-3-hydroxy-2-methyl-5-phenylmethoxypentanal | 1008781-49-4

• 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)-3-hydroxy-2-methyl-5-phenylmethoxypentanal
• CAS: 1008781-49-4
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: DYONFPOSXHOIOH-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-hydroxy-2-methyl-5-phenylmethoxypentanal 在 甲醇 、 magnesium 作用下， 反应 8.0h， 生成 (4S,5S)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylheptanoate
  参考文献：
  名称：

  Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A

  摘要：

  A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.085
• 作为产物：
  描述：

  3-苄氧基丙醛 在 sodium tetrahydroborate 、 bis(acetoxy)iodobenzene 、 2,2,6,6-四甲基哌啶氧化物 、 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2R,3S)-3-hydroxy-2-methyl-5-phenylmethoxypentanal
  参考文献：
  名称：

  Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A

  摘要：

  A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.085

文献信息

• An improved synthesis of (−)-brevisamide, a marine monocyclic ether amide of dinoflagellate origin
  作者：Ryosuke Tsutsumi、Takefumi Kuranaga、Jeffrey L.C. Wright、Daniel G. Baden、Emiko Ito、Masayuki Satake、Kazuo Tachibana

  DOI：10.1016/j.tet.2010.06.074

  日期：2010.8

  An improved synthesis of (−)-brevisamide a marine cyclic ether isolated from the red-tide dinoflagellate Karenia brevis was achieved. The ether ring portion was constructed from an unsaturated lactone, which was prepared enantioselectively via an Evans aldol reaction and one-pot lactonization in the presence of excessive base after an Ando reaction. The ether ring and a dienol side chain fragment were

  实现了一种改进的合成方法，该方法合成了从赤潮双鞭毛贝氏克雷尼亚氏菌中分离出来的海洋环醚（-）-brevisamide 。醚环部分由不饱和内酯构成，该不饱和内酯通过Evans aldol反应和在Ando反应后在过量碱的存在下一锅内酯化而对映选择性地制备。醚环和二烯醇侧链片段通过Suzuki-Miyaura偶联连接。
• A general synthetic approach for the synthesis of β-hydroxy-δ-lactones: asymmetric total synthesis of prelactones and epi-prelactones V and E
  作者：Gowravaram Sabitha、P. Padmaja、K. Bhaskar Reddy、J.S. Yadav

  DOI：10.1016/j.tetlet.2007.11.080

  日期：2008.1

  A general synthetic approach for the synthesis of prelactones and epi-prelactones V and E has been reported using an Evans’ aldol reaction as the key step.

  已经报道了使用埃文斯的醛醇缩合反应作为关键步骤来合成prelactones和epi- prelactones V和E的通用合成方法。
• Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A
  作者：Jhillu Singh Yadav、Eppa Gyanchander、Anand Kumar Mishra、Peddapuram Adithya、Saibal Das

  DOI：10.1016/j.tetlet.2013.08.085

  日期：2013.10

  A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.