syringolide 2 3-O-methyl ether | 166543-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: syringolide 2 3-O-methyl ether
• 英文别名: 3-O-methylsyringolide 2；3-Methoxysyringolide 2；(1R,4R,5S,7R,8S)-7-heptyl-4-hydroxy-7-methoxy-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-9-one
• CAS: 166543-04-0
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: NTRNPBJEOLSWMQ-VRUQUDLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  syringolide 2 3-O-methyl ether 在 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 以51%的产率得到(-)-syringolide
  参考文献：
  名称：

  丁香假单胞菌pv引发剂丁香酚内酯2的合成和绝对构型。番茄

  摘要：

  丁香假单胞菌pv产生的两个激发子之一的丁香酚内酯2的对映体选择性合成。从酒石酸二乙酯分11步完成番茄。

  DOI：

  10.1016/0040-4039(95)00512-b
• 作为产物：
  描述：

  3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-4-(1-hydroxyoctyl)-2H-furan-5-one 在 Dowex 50W-8X 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 生成 syringolide 2 3-O-methyl ether
  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

• Synthesis of (−)-syringolides 1 and 2
  作者：Shigefumi Kuwahara、Masahiko Moriguchi、Kazuhiro Miyagawa、Masako Konno、Osamu Kodama

  DOI：10.1016/0040-4020(95)00488-t

  日期：1995.8

  enantioselective synthesis of (−)-syringolides 1 and 2 which were isolated as specific elicitors produced by Pseudomonas syringae pv. tomato was accomplished in 11 steps from diethyl d tartrate. The specific rotations of synthetic samples were in good accord with those of the natural syringolides, and synthetic syringolide 2 showed almost the same biological activity as that of natural syringolide 2.

  （-）-丁香油酸酯1和2的对映选择性合成，其作为丁香假单胞菌pv产生的特定引发剂被分离。从酒石酸二乙酯分11步完成番茄。合成样品的比旋光度与天然丁香酚的旋光度非常一致，合成丁香酚2的生物活性几乎与天然丁香酚2的生物活性相同。
• The structures of syringolides 1 and 2, novel C-glycosidic elicitors from Pseudomonas syringae pv. tomato
  作者：Sharon L. Midland、Noel T. Keen、James J. Sims、M. Mark Midland、Mark M. Stayton、Vicki Burton、Mitchell J. Smith、Eugene P. Mazzola、Kate J. Graham、Jon Clardy

  DOI：10.1021/jo00063a007

  日期：1993.5

  The isolation and structure determination of two bacterial signal molecules which elicit active plant defense responses are reported. The production of these molecules by Gram-negative bacteria requires the action of a virulence gene D (avrD), cloned from Pseudomonas syringae pv. tomato. The structures of syringolide 1 (1a) and syringolide 2 (1b) are determined by a combination of NMR experiments, biosynthetic arguments, molecular modeling, and X-ray crystallography. A proposed biosynthetic scheme based on the condensation of D-xylulose with a beta-ketoalkanoic acid is presented. Further cyclization of the biosynthetic intermediates leads to C-glycosides with a novel tricyclic ring system. These are the first nonproteinaceous specific elicitors of a plant hypersensitive response.