3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2H-furan-5-one | 184780-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2H-furan-5-one
• CAS: 184780-79-8
• 化学式: C₁₆H₂₈O₅Si
• 分子量: 328.481
• InChiKey: QGOCFEOKIUWENG-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2H-furan-5-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以85%的产率得到(1'R,2'R)-3-[1'-hydroxy-2',3'-(isopropylidenedioxy)propyl]but-2-en-4-olide
  参考文献：
  名称：

  Total Syntheses of Sphydrofuran, Secosyrins, and Syributins^,1

  摘要：

  Two groups of natural products, sphydrofuran (1) and its furan derivative (2) and secosyrins 1 and 2 (3a, 3b) and syributins 1 and 2 (4a, 4b), were synthesized from one precursor (6), which was realized starting from 3-tri-n-butylstannylfuran or 3-bromofuran.

  DOI：

  10.1021/jo970476+
• 作为产物：
  描述：

  3-[(1R,2R)-3-[tert-butyl(dimethyl)silyl]oxy-1,2-dihydroxypropyl]-2H-furan-5-one 在 咪唑 、 4-甲基苯磺酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2H-furan-5-one
  参考文献：
  名称：

  Enantioselective Syntheses of Syributin 1 and Novel C-Glycosidic Elicitors Syringolides 1 and 2

  摘要：

  Concise enantioselective syntheses of syributin 1 (3) and the novel nonproteinaceous C-glycosidic elicitors syringolides 1 and 2 (1 and 2, respectively), isolated from Pseudomonas syringae pv. tomato, are described. Syributin 1 was synthesized in one step by the Sharpless catalytic asymmetric dihydroxylation (AD reaction) of (1'E)-3-(3'-(octanoyloxy)-1'-propenyl)but-2-en-4-olide (13) in 72% yield with >98% ee. Furthermore, alkylation of (1'R,2'R)-3-[1'-(tert-butyldimethylsiloxy)-2,3'- (isopropylidenedioxy)propyl]but-2-en-4-olide (20), prepared from (1'E)-3-[3'-(tert-butyldimethylsiloxy)-1'-propenyl]but-2-en-4-olide (11) by the AD reaction, with hexanal or octanal by Jefford's procedure at the a position to the lactone carbonyl group gave adduct 21 or 22 in good yield. Oxidation of 21 or 2;2, followed by removal of the protecting groups, provided syringolide 1 or 2, respectively.

  DOI：

  10.1021/jo961362l

文献信息

• An improved synthesis of (−)-syringolides and X-ray structural characterization of synthetic (−)-syringolide 1
  作者：Pei Yu、Qi-Guang Wang、Thomas C.W. Mak、Henry N.C. Wong

  DOI：10.1016/s0040-4020(97)10401-x

  日期：1998.2

  On treatment with 10% HF, butenolides 4a and 4b afforded enantiopure (−)-syringolides 1 (1a) and 2 (1b) respectively in much higher yields. Unprecedentedly, the cyclic acetal 5a was also converted to 1a by reacting with an excess of p-TsOH. The structure of the synthetic (−)-syringolide 1 (1a) was substantiated by an X-ray crystallographic study.

  在用10％HF处理时，丁烯内酯4a和4b分别以高得多的产率提供了对映纯（-）-丁香油酯1（1a）和2（1b）。前所未有地，通过与过量的p-TsOH反应，环状缩醛5a也被转化为1a。通过X射线晶体学研究证实了合成的（-）-丁香油精1（1a）的结构。