3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-4-(1-hydroxyhexyl)-2H-furan-5-one | 184780-81-2

• 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]-4-(1-hydroxyhexyl)-2H-furan-5-one
• CAS: 184780-81-2
• 化学式: C₂₂H₄₀O₆Si
• 分子量: 428.641
• InChiKey: SEWWDHYZKWLKLB-DOGRWBMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

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]-4-(1-hydroxyhexyl)-2H-furan-5-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-4-hexanoyl-2H-furan-5-one
  参考文献：
  名称：

  （-）-丁香油精的合成方法改进和合成（-）-丁香油精1的X射线结构表征

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(97)10401-x
• 作为产物：
  描述：

  (1'R,2'R)-3-[1'-hydroxy-2',3'-(isopropylidenedioxy)propyl]but-2-en-4-olide 在 咪唑 、 Bu₄BOTf 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-4-(1-hydroxyhexyl)-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

• Enantioselective Syntheses of Syributin 1 and Novel C-Glycosidic Elicitors Syringolides 1 and 2
  作者：Toshio Honda、Hirotake Mizutani、Kazuo Kanai

  DOI：10.1021/jo961362l

  日期：1996.1.1

  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.
• 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。