(1′R,5R)-5-(1′,2′-dihydroxyethyl)dihydrofuran-2(3H)-one | 161906-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1′R,5R)-5-(1′,2′-dihydroxyethyl)dihydrofuran-2(3H)-one
• 英文别名: 2,3-dideoxy-D-threo-hexono-1,4-lactone；(4R,5R)-5,6-dihydroxy-4-hexanolide；(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolan-2-one
• CAS: 161906-46-3
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: WKCBOODKPXKQAC-RFZPGFLSSA-N

物化性质

• 沸点：
  410.9±15.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1′R,5R)-5-(1′,2′-dihydroxyethyl)dihydrofuran-2(3H)-one 在 sodium tetrahydroborate 、 sodium periodate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.67h， 生成 (R)-γ-羟甲基-γ-丁内酯 (R)-4,5-二氢-5-羟甲基-2(3H)-呋喃酮 (R)-5-羟甲基-2-氧代四氢呋喃
  参考文献：
  名称：

  Unexpected Stereochemistry in the Lithium Salt Catalyzed Ring Expansion of Nonracemic Oxaspiropentanes. Formal Syntheses of (−)-(4R,5R)-Muricatacin and the Pheromone (R)-Japonilure

  摘要：

  The stereochemistry of the cyclobutanones 3, obtained by lithium salt catalyzed ring expansion of the optically pure oxaspiropentanes 2, depends not only on the lithium salt but also on the stereochemistry of 2. They constitute the starting material for the syntheses of the acetogenin (-)-(4R,5R)-muricatacin and the pheromone (R)-japonllure.

  DOI：

  10.1021/ol035061r
• 作为产物：
  描述：

  5-O-benzyl-2,3-dideoxy-D-threo-hexono-1,4-lactone 在 palladium on activated charcoal 甲醇 、 三氟乙酸 、 氢气 作用下， 反应 20.5h， 生成 (1′R,5R)-5-(1′,2′-dihydroxyethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  d-木糖的对映体纯羟基内酯。适用于制备7-氧杂类似物的（+）-和（-）-多卡他霉素对映异构合成的新方法

  摘要：

  从d-木糖开始，已开发出一种新的途径，以对映体纯的羟基内酯3和ent - 3为对映体合成（+）-和（-）-多卡他霉素的最终手性前体。

  DOI：

  10.1016/j.tetlet.2003.09.168

文献信息

• Enantiopure hydroxylactones from L-ascorbic and D-isoascorbic acids. Part I. Synthesis of (−)-muricatacin
  作者：Michèle Sanière、Isabelle Charvet、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1016/0040-4020(94)01032-u

  日期：1995.2

  From D-isoascorbic acid, via a formal bis-epoxide equivalent with a C-2 axis of symmetry, two possible syntheses of the (−)-Muricatacin are described.

  从D-异抗坏血酸，通过具有C-2对称轴的形式双环氧化合物，描述了（-）-Muricatacin的两种可能的合成方法。
• Enantiopure hydroxylactones from d-xylose. A novel approach to the enantiodivergent synthesis of (+)- and (−)-muricatacin suitable for the preparation of 7-oxa analogues
  作者：Velimir Popsavin、Ivana Krstić、Mirjana Popsavin

  DOI：10.1016/j.tetlet.2003.09.168

  日期：2003.12

  A new route towards enantiopure hydroxylactones 3 and ent-3, the final chiral precursors in an enantiodivergent synthesis of (+)- and (−)-muricatacin, has been developed starting from d-xylose.

  从d-木糖开始，已开发出一种新的途径，以对映体纯的羟基内酯3和ent - 3为对映体合成（+）-和（-）-多卡他霉素的最终手性前体。
• Synthesis of (-)-Muricatacin from Tri-O-acetyl-d-glucal
  作者：Generosa Gómez、Yagamare Fall、Maria González、Zoila Gándara、Gonzalo Pazos

  DOI：10.1055/s-0032-1318113

  日期：——

  The total synthesis of (-)-muricatacin is achieved using commercially available tri-O-acetyl-D-glucal as the starting material. The structure of the intermediate chiral butenolide is established unambiguously by X-ray crystallographic analysis, which consequently leads to correction of a previous structural misassignment.
• Unexpected Stereochemistry in the Lithium Salt Catalyzed Ring Expansion of Nonracemic Oxaspiropentanes. Formal Syntheses of (−)-(4<i>R</i>,5<i>R</i>)-Muricatacin and the Pheromone (<i>R</i>)-Japonilure
  作者：Angela M. Bernard、Angelo Frongia、Pier P. Piras、Francesco Secci

  DOI：10.1021/ol035061r

  日期：2003.8.1

  The stereochemistry of the cyclobutanones 3, obtained by lithium salt catalyzed ring expansion of the optically pure oxaspiropentanes 2, depends not only on the lithium salt but also on the stereochemistry of 2. They constitute the starting material for the syntheses of the acetogenin (-)-(4R,5R)-muricatacin and the pheromone (R)-japonllure.
• Enantiodivergent synthesis of muricatacin related lactones from d-xylose based on the latent symmetry concept: preparation of two novel cytotoxic (+)- and (−)-muricatacin 7-oxa analogs
  作者：Velimir Popsavin、Ivana Krstić、Mirjana Popsavin、Bojana Srećo、Goran Benedeković、Vesna Kojić、Gordana Bogdanović

  DOI：10.1016/j.tet.2006.09.054

  日期：2006.11

  Enantiodivergent formal synthesis of (+)- and (−)-muricatacins from d-xylose has been accomplished through utilization of the latent plane of symmetry present in the starting monosaccharide. This approach was extended to the preparation of two novel (+)- and (−)-muricatacin 7-oxa analogs (2 and ent-2, respectively), which showed in vitro antitumor activity toward some human malignant cells. The analog

  通过利用存在于起始单糖中的对称性潜平面，已完成了由d-木糖对映体形式的（+）-和（-）-穆里卡他星的对映体形式合成。该方法扩展到制备两种新颖的（+）-和（-）-多卡他霉素7-oxa类似物（分别为2和ent - 2），它们显示出对某些人类恶性细胞的体外抗肿瘤活性。类似物ent - 2对K562细胞系显示出强大的抗增殖活性，效力比标准细胞毒剂阿霉素高36倍。化合物2然而，它对HL-60细胞显示出强大的细胞毒活性，相对于参比化合物，其效力高17倍以上。