(5S)-5-(furan-3-yl)-5-hydroxy-3-oxo-pentanoic acid | 267649-62-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (5S)-5-(furan-3-yl)-5-hydroxy-3-oxo-pentanoic acid
• 英文别名: 5-(S)-[furan-3-yl]-5-hydroxy-3-oxo-pentanoic acid methyl ester；(5S)-methyl 5-[furan-3-yl]-5-hydroxy-3-oxopentanoate；methyl (5S)-5-(furan-3-yl)-5-hydroxy-3-oxopentanoate
• CAS: 267649-62-7
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: YAJHFXJSMLQLLG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S)-5-(furan-3-yl)-5-hydroxy-3-oxo-pentanoic acid 在 lithium hydroxide 、 sodium hydroxide 、 zinc(II) tetrahydroborate 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 乙醇 为溶剂， 反应 4.0h， 生成 (6S)-(furan-3-yl)-4-acetoxy-3-methyltetrahydropyran-2-one
  参考文献：
  名称：

  Stereochemistry of Antiinflammatory Marine Sesterterpenes

  摘要：

  DOI：

  10.1002/(sici)1099-0690(200003)2000:6<947::aid-ejoc947>3.0.co;2-u
• 作为产物：
  描述：

  (S)-5-Furan-3-yl-3-oxo-5-trimethylsilanyloxy-pentanoic acid methyl ester 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 (5S)-5-(furan-3-yl)-5-hydroxy-3-oxo-pentanoic acid
  参考文献：
  名称：

  Enantioselective aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene promoted by chiral Ti(IV)/BINOL complex

  摘要：

  Enantiomerically enriched delta-hydroxy-beta-ketoesters are easily available by aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene in the presence of Ti(O-iPr)(4)/(S)-(-)-BINOL system. All reaction mixtures were separated by column chromatography and mostly isolated in moderate to good yields and all in high enantiomeric excesses. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00200-7

文献信息

• Enantioselective Synthesis of Pyranofuranone Moieties of Manoalide and Cacospongionolide B by Enzymatic and Chemical Approach
  作者：Margherita De Rosa、Annunziata Soriente、Guido Sodano、Arrigo Scettri

  DOI：10.1016/s0040-4020(00)00122-8

  日期：2000.3

  Two synthetic sequences leading to the pyranofuranone moieties of Manoalide and Cacospongionolide B in enantiomerically enriched forms are reported. The key steps involve either an enantioselective aldol condensation or an enzymatic resolution.

  报道了导致对映异构体富集形式的Manoalide和Cacospongionolide B的吡喃呋喃酮部分的两个合成序列。关键步骤涉及对映选择性羟醛缩合或酶促拆分。
• A new procedure for the enantioselective vinylogous aldol reaction of Chan’s diene
  作者：Rosaria Villano、Maria Rosaria Acocella、Antonio Massa、Laura Palombi、Arrigo Scettri

  DOI：10.1016/j.tetasy.2006.12.016

  日期：2006.12

  Chiral delta-hydroxy-delta-ketoesters are easily available through the enantio selective vinylogous aldol reaction of Chan's diene promoted by a SiCl4/chiral phosphoramide catalytic system. The procedure is conveniently exploited for a very rapid approach to (+)-kavain, a natural bio-active alpha-pyrone compound. (c) 2007 Elsevier Ltd. All rights reserved.
• An easy approach to chiral non-racemic 6-(furan-3-yl)-5,6-dihydro-pyran-2-ones
  作者：Annunziata Soriente、Margherita De Rosa、Patrizia Dovinola、Guido Sodano、Arrigo Scettri

  DOI：10.1016/s0957-4166(98)00210-9

  日期：1998.7

  Chiral non-racemic 6-(furan-3-yl)-pyran-2-one derivatives, key-intermediates in the preparation of compactin, manoalide and cacospongionolide subunits, are easily accessible through a rapid and convenient six-step sequence. (C) 1998 Elsevier Science Ltd. All rights reserved.