(S)-5-((1S,2R,3S)-1,2,3-trihydroxy-3-phenylpropyl)furan-2(5H)-one | 164668-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (S)-5-((1S,2R,3S)-1,2,3-trihydroxy-3-phenylpropyl)furan-2(5H)-one
• 英文别名: (5S)-5-[(1S,2R,3S)-1,2,3-trihydroxy-3-phenylpropyl]furan-2(5H)-one；(2S)-2-[(1S,2R,3S)-1,2,3-trihydroxy-3-phenylpropyl]-2H-furan-5-one
• CAS: 164668-41-1
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: FJBARMGOBUNTIH-FTYKPCCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-5-((1S,2R,3S)-1,2,3-trihydroxy-3-phenylpropyl)furan-2(5H)-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以68%的产率得到(+)-7-epi-goniofufurone
  参考文献：
  名称：

  生物活性苯乙烯内酯的立体选择性全合成：9-Deoxygoniopypyrone、Goniopypyrone 和 7-epi-Goniofufurone

  摘要：

  生物活性苯乙烯内酯 (+)-9-deoxygoniopypyrone、(+)-goniopypyrone 和 (+)-7-epi-goniofufurone 的立体选择性合成已由 d-(-)-酒石酸实现。关键步骤涉及利用高产立体选择性转化将三羟基酯制备成标题化合物。

  DOI：

  10.1055/s-2007-990866
• 作为产物：
  描述：

  ethyl (2S,3S,4R)-4-(t-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl butanoate 在 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 四丁基氟化铵 、 potassium carbonate 、 溶剂黄146 、 triethylamine tris(hydrogen fluoride) 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 256.0h， 生成 (S)-5-((1S,2R,3S)-1,2,3-trihydroxy-3-phenylpropyl)furan-2(5H)-one
  参考文献：
  名称：

  抗肿瘤药（+）-goniopypyrone和（+）-7- epi- goniofufurone的全合成

  摘要：

  对映纯（+）-7-表位-呋喃酮，1和（+）-吡喃酮2的合成已从C-4碳链Chiron 3中获得，而C-4碳Chiron 3可从（R）-扁桃酸中轻易获得。

  DOI：

  10.1016/s0040-4039(96)02439-2

文献信息

• An Expeditious Enantiospecific Total Synthesis of (+)-7-<i>epi</i>-Goniofufurone
  作者：Kavirayani R. Prasad、Shivajirao L. Gholap

  DOI：10.1055/s-2005-871965

  日期：——

  Stereoselective synthesis of styryl lactone, (+)-7-epi-goniofufurone was achieved in high yield via simple transformations from tartaric acid. The key step involves the successive stereoselective reduction of ketones with borohydride and selectride.

  立体选择性合成苯乙烯内酯(+)-7-epi-goniofufurone通过对酒石酸的简单转化获得高产率。关键步骤涉及对酮的连续立体选择性还原，使用硼氢化钠和选择性还原剂。
• Gonibutenolides A and B: serendipitous syntheses, relative and absolute configuration
  作者：Tony K. M. Shing、Vincent W.-F. Tai、Hon-Chung Tsui

  DOI：10.1039/c39940001293

  日期：——

  The relative and absolute stereochemistries of natural goniobutenolides A and B are established as 1 and 2 respectively by short syntheses of them and their 8-epimers.

  通过简短合成天然高尼丁内酯 A 和 B 及其 8-表聚物，确定它们的相对和绝对立体化学结构分别为 1 和 2。
• Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-<i>epi</i>-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin
  作者：Kavirayani R. Prasad、Shivajirao L. Gholap

  DOI：10.1021/jo0702342

  日期：2008.1.1

  [GRAPHICS]Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from D-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of gamma-phenyl-gamma-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.
• Enantiospecific Syntheses of (+)-Goniofufurone, (+)-7-epi-Goniofufurone, (+)-Goniobutenolide A, (-)-Goniobutenolide B, (+)-Goniopypyrone, (+)-Altholactone, (+)-Goniotriol, and (+)-7-Acetylgoniotriol
  作者：Tony K. M. Shing、Hon-Chung Tsui、Zhao-Hui Zhou

  DOI：10.1021/jo00115a030

  日期：1995.5

  Practical and efficient syntheses of a number of styryl lactones with various structural complexities were accomplished from commercially available and inexpensive D-glycero -D-gulo-heptono-gamma-lactone (D-glucoheptonic gamma-lactone)(11). Lactone 11 was converted by four sequential reactions (acetonation, selective deacetonation, glycol cleavage oxidation, and Grignard reaction) into key intermediates 3,5-O-isopropylidene-1, 1,6-tri-C-phenyl-D-glycero-D-gulo-hexitol (15) and 3,5-O-isopropylidene-1,1,6-tri-C-phenyl-L-glycero-D-gulo- hexitol(16). The alcohol 15 was transformed via a glycol cleavage oxidation and a Z-selective Wittig reaction into enoate Z-9 which underwent hydrolysis and an intramolecular Michael-type cyclization to give (+)-goniofufurone (1). Likewise, reaction of 16 afforded 7-epi-goniofufurone (2). Acylation and subsequent deacylation of 7-C-phenyl-D-gluco-hept-2-enono-gamma-lactone (20) readily gave (+)-goniobutenolide A (3) and (-)-goniobutenolide B (4), whereas treatment of (Z)-methyl 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enonate (Z-22) with DBU followed by acid hydrolysis and intramolecular Michael reaction provided (+)-goniopypyrone (5). Mesylation of 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enono-delta- lactone (27) followed by acid hydrolysis furnished (+)-altholactone (6). (+)-Goniotriol (7) and (+)-7-acetylgoniotriol (8) were readily obtained from the enoate Z-9. This work also provides a viable synthetic route for the construction of the enantiomers of the above styryl lactones for biological evaluation from the same starting material 11. Suggestions about the possible biosynthetic pathway of the styryl lactones are given.