(2R,3R,3aS,7R,7aS)-3,7-dihydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one | 139626-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (2R,3R,3aS,7R,7aS)-3,7-dihydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one
• 英文别名: (2R,3R,3aS,7R,7aS)-3,7-dihydroxy-2-phenylhexahydro-5H-furo[3,2-b]pyran-5-one；(1S,5R,6S,8R,9R)-5,9-dihydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one；(-)-goniofupyrone；goniofupyrone；(2R,3R,3aS,7R,7aS)-3,7-dihydroxy-2-phenyl-2,3,3a,6,7,7a-hexahydrofuro[3,2-b]pyran-5-one
• CAS: 139626-38-3
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: GYCYBXCAAVSCJA-XTAFZBPGSA-N

物化性质

• 沸点：
  540.2±50.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,3aS,7R,7aS)-3,7-dihydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one 在 4-二甲氨基吡啶 、 硫酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (1'R^*,2S^*,3S^*,4S^*,5R^*)-3,4-diacetoxy-2-<(1'-acetoxy-2'-methoxylcarbonyl)ethyl>-5-phenyltetrahydrofuran
  参考文献：
  名称：

  Revised Structure of Gonioheptolide A.

  摘要：

  (±)-Gonioheptolide A (3) was unambiguously synthesized from (±)-goniofupyrone (4) and thereby its structure was revised as (1'R*, 2S*, 3S*, 4S*, 5R*)-3, 4-dihydroxy-2-[(1'-hydroxy-2'-methoxycarbonyl)ethyl]-5-phenyl-tetrahydrofuran. Methanolysis of (±)-goniofupyrone (4) with conc.H2SO4 at room temperature provided (±)-gonioheptolide A (3) in 48% yield. The synthetic (±)-gonioheptolide A and its triacetate were comparable to natural gonioheptolide A and its triacetate, respectively.

  DOI：

  10.1248/cpb.47.131
• 作为产物：
  描述：

  (2R,3R,3aS,7R,7aS)-3-Benzyloxy-5-methoxy-2-phenyl-hexahydro-furo[3,2-b]pyran-7-ol 在 lithium aluminium tetrahydride 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 三氟化硼乙醚 、 四氯化锡 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 (2R,3R,3aS,7R,7aS)-3,7-dihydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one
  参考文献：
  名称：

  （-）-goniofupyrone的第一个全合成和结构解析

  摘要：

  （ - ） -的第一全合成goniofupyrone，分离自哥纳香属巨，在从（+）立体选择性方式实现-三羰基（η 6 -2- trimethylsilylbenzaldehyde） -铬（0）络合物。该合成明确地建立了（-）-goniofupyrone的相对和绝对立体化学。

  DOI：

  10.1016/0040-4039(96)01085-4

文献信息

• Stereoselective Synthesis of (+)-Goniodiol, (+)-Goniotriol, (-)-Goniofupyrone, and (+)-Altholactone Using a Catalytic Asymmetric Hetero-Diels-Alder/Allylboration Approach
  作者：Annaïck Favre、François Carreaux、Michael Deligny、Bertrand Carboni

  DOI：10.1002/ejoc.200800535

  日期：2008.10

  The stereoselective total synthesis of several members of the styryllactone family was achieved efficiently from common intermediate 8, prepared by a catalytic asymmetric inverse-electron-demand hetero-Diels–Alder/allylboration sequence. The transformation of 8 into α,β-unsaturated lactone led to the preparation of (+)-goniodiol (1) in a reduced number of steps. The epoxidation reaction was used to

  苯乙烯内酯家族的几个成员的立体选择性全合成是从普通中间体 8 有效地实现的，中间体 8 通过催化不对称逆电子需求异质狄尔斯-阿尔德/烯丙基硼化序列制备。将 8 转化为 α,β-不饱和内酯导致以减少的步骤数制备 (+)-goniodiol (1)。环氧化反应用于在 8 的内酯部分产生剩余的立体中心，然后将这些中间体加工成 (+)-goniotriol (2)、(-)-goniofupyrone (3) 和 (+)-altholactone ( 4) 通过异构化或环化步骤。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Semisynthesis of new tetrahydrofuranic alkyl ester and furano-pyrone derivatives as inhibitors of the mitochondrial complex I
  作者：Eva Peris、Adrien Cavé、Ernesto Estornell、M.Carmen Zafra-Polo、Bruno Figadère、Diego Cortes、Almudena Bermejo

  DOI：10.1016/s0040-4020(01)01234-0

  日期：2002.2

  altholactone (1) led to the corresponding O-methoxymethyl derivative (3) in addition to the unexpected 6,7-dihydro-7-methoxy analogue (4), and two original tetrahydrofuranic (THF) alkyl esters ( 5,6). Moreover, when we accomplished a new method for the preparation of the furano-pyrone goniofupyrone (7) through 7-hydroxylation of 1 in acid medium, a minor compound (8) with an identical skeleton to that of compounds

  altholactone的甲氧基甲基（1）导致了相应ø -甲氧基甲基衍生物（3）除了意外6,7-二氢-7-甲氧基类似物（4），和两个原始tetrahydrofuranic（THF）烷基酯（5，6） 。此外，当我们完成了一种通过在酸性介质中将1进行7-羟基化来制备呋喃并吡喃酮goniofupyrone（7）的新方法时，一种骨架与化合物5和6相同的次要化合物（8）。被确定。仔细检查已报道的具有庚内酯骨架的苯乙烯基内酯的光谱数据，发现这些结构也具有THF烷基酯骨架。通过化学相关性证实了那些结构的修饰。所有测定的内酯衍生物均证明是线粒体复合体I的特异性抑制剂。
• First Total Synthesis and Absolute Configuration of the Styryl Lactone Gonioheptolide A
  作者：Richard Hudson、Shuchi Gupta、Murali Rajagopalan、Mamoun Alhamadsheh、L. Tillekeratne

  DOI：10.1055/s-2007-990862

  日期：2007.11

  Efficient asymmetric syntheses of both naturally occurring and non-naturally occurring enantiomers of gonioheptolide A are reported. The absolute configuration of (+)-gonioheptolide A was established by NOESY, Mosher ester analysis, and comparison with the specific rotation of the isolated (+)-gonioheptolide A.

  报道了天然和非天然的戈尼庚醇A对映异构体的高效不对称合成。通过NOESY、Mosher酯分析以及与分离得到的(+)-戈尼庚醇A的特定旋光度进行比较，确立了(+)-戈尼庚醇A的绝对构型。
• The first total synthesis of (+)-goniothalesacetate and syntheses of (+)-altholactone, (+)-gonioheptolide A, and (−)-goniofupyrone by an asymmetric acetate aldol approach
  作者：Sandeep AnkiReddy、Praveen AnkiReddy、Gowravaram Sabitha

  DOI：10.1039/c5ob01598g

  日期：——

  The first stereoselective total synthesis of (+)-goniothalesacetate and total synthesis of several bioactive styryl lactones, (+)-altholactone, (+)-gonioheptolide A, and (−)-goniofupyrone have been achieved from an advanced intermediate, which can be derived from L-(+)-DET.

  （+）-goniothalesacetate的第一个立体选择性全合成和几种生物活性苯乙烯基内酯，（+）-甲内酯，（+）-gonioheptolide A和（-）-goniofupyrone的全合成已经可以从一种先进的中间体中获得。衍生自L -（+）-DET。
• Stereoselective Syntheses of (+)-Goniotriol, (+)-8-Acetylgoniotriol, (+)-Goniodiol, (+)-9-Deoxygoniopypyrone, (+)-Altholactone, and (−)-Goniofupyrone
  作者：Chisato Mukai、Syuichi Hirai、Miyoji Hanaoka

  DOI：10.1021/jo970725u

  日期：1997.9.1

  The gamma-lactone intermediate (-)-7, derived from (+)-tricarbonyl(eta(6)-o-(trimethylsilyl)benzaldehyde)chromium (O) complex, was efficiently converted into the corresponding delta-lactone intermediate (-)-11. This second intermediate has been shown to be a versatile compound for stereoselective syntheses of natural styryllactones possessing a six-membered lactone moiety, isolated from Goniothalamus giganteus, by transforming it into (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniodiol, (+)-9-deoxygoniopypyrone, (+)-altholactone, and (-)-goniofupyrone.