(R)-3-Methyl-4-((R)-4-oxo-3,4-dihydro-2H-pyran-2-yl)-butyric acid methyl ester | 438222-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (R)-3-Methyl-4-((R)-4-oxo-3,4-dihydro-2H-pyran-2-yl)-butyric acid methyl ester
• 英文别名: methyl (3R)-3-methyl-4-[(2R)-4-oxo-2,3-dihydropyran-2-yl]butanoate
• CAS: 438222-46-9
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: OKLHFCSWXCTOCM-PSASIEDQSA-N

物化性质

• 沸点：
  286.6±9.0 °C(predicted)
• 密度：
  1.089±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-Methyl-4-((R)-4-oxo-3,4-dihydro-2H-pyran-2-yl)-butyric acid methyl ester 在 四(三苯基膦)钯 、 正丁基锂 、 cerium(III) chloride 、 四甲基乙二胺 、 D-tartaric acid derivative 、 四丁基氟化铵 、 三正丁基氢锡 、 silica gel 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 127.87h， 生成 4-[(2R,6R)-6-((E)-(2S,6S,10S,11S)-10,11-Dihydroxy-6-methoxymethoxy-2-methyl-4-methylene-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-ynoic acid
  参考文献：
  名称：

  Pharmacophore Mapping in the Laulimalide Series:  Total Synthesis of a Vinylogue for a Late-Stage Metathesis Diversification Strategy

  摘要：

  An efficient synthesis of the macrocyclic core of laulimalide with a pendant vinyl group at C20 is described, allowing for late-stage introduction of various side chains through a selective and efficient cross metathesis diversification step. Representative analogues reported herein are the first to contain modifications to only the side chain dihydropyran of laulimalide and des-epoxy laulimalide. This step-economical strategy enables the rapid synthesis of new analogues using alkenes as an inexpensive, abundantly available diversification feedstock.

  DOI：

  10.1021/ol061619u
• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 methyl (3R)-3-methyl-5-oxopentanoate 在 R,R-Jacobsen's catalyst 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 、 (R)-3-Methyl-4-((R)-4-oxo-3,4-dihydro-2H-pyran-2-yl)-butyric acid methyl ester
  参考文献：
  名称：

  Synthesis of (−)-laulimalide: an agent for microtubule stabilization

  摘要：

  An enantioselective synthesis or (-)-laulimalide is described. Key reactions include a convergent allylation coupling reaction, asymmetric conjugate addition, the allenylstannane Ferrier reaction and a chelation-controlled alkenylzine addition as the basis for stereocontrol in critical elements of chirality. (C) 20021 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00907-3

文献信息

• LAULIMALIDE AND LAULIMALIDE ANALOGS
  申请人：WENDER PAUL A.

  公开号：US20080227851A1

  公开（公告）日：2008-09-18

  Novel laulimalide analogs, methods for the treatment of proliferative disease and processes for the synthesis of laulimalide and novel laulimalide analogs are described.

  描述了新型laulimalide类似物、治疗增殖性疾病的方法以及合成laulimalide和新型laulimalide类似物的过程。
• Synthesis of (−)-laulimalide: an agent for microtubule stabilization
  作者：David R. Williams、Liang Mi、Richard J. Mullins、Ryan E. Stites

  DOI：10.1016/s0040-4039(02)00907-3

  日期：2002.7

  An enantioselective synthesis or (-)-laulimalide is described. Key reactions include a convergent allylation coupling reaction, asymmetric conjugate addition, the allenylstannane Ferrier reaction and a chelation-controlled alkenylzine addition as the basis for stereocontrol in critical elements of chirality. (C) 20021 Elsevier Science Ltd. All rights reserved.
• Pharmacophore Mapping in the Laulimalide Series:  Total Synthesis of a Vinylogue for a Late-Stage Metathesis Diversification Strategy
  作者：Paul A. Wender、Michael K. Hilinski、Philip R. Skaanderup、Nicolas G. Soldermann、Susan L. Mooberry

  DOI：10.1021/ol061619u

  日期：2006.8.1

  An efficient synthesis of the macrocyclic core of laulimalide with a pendant vinyl group at C20 is described, allowing for late-stage introduction of various side chains through a selective and efficient cross metathesis diversification step. Representative analogues reported herein are the first to contain modifications to only the side chain dihydropyran of laulimalide and des-epoxy laulimalide. This step-economical strategy enables the rapid synthesis of new analogues using alkenes as an inexpensive, abundantly available diversification feedstock.