(1R,4R,5S,7R,8S)-4-hydroxy-7-methoxy-7-pentyl-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-9-one | 170937-99-2

• 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: (1R,4R,5S,7R,8S)-4-hydroxy-7-methoxy-7-pentyl-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-9-one
• CAS: 170937-99-2
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: VVBJJRZHRGVSPD-VSEIDBEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (1R,4R,5S,7R,8S)-4-hydroxy-7-methoxy-7-pentyl-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-9-one 在 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 以46%的产率得到syringolide 1
  参考文献：
  名称：

  （-）-丁香油酸酯1和2的合成

  摘要：

  （-）-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。

  DOI：

  10.1016/0040-4020(95)00488-t
• 作为产物：
  描述：

  3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2H-furan-5-one 在 Bu₄BOTf 、 Dowex 50W-8X 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 (1R,4R,5S,7R,8S)-4-hydroxy-7-methoxy-7-pentyl-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-9-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

• Formal Synthesis of (-)-Syringolide 1 Starting from D-Xylose Based on a Biomimetic Strategy
  作者：Hidemi Yoda、Miho Kawauchi、Kunihiko Takabe、Ken Hosoya

  DOI：10.3987/com-97-7926

  日期：——

  An expeditious and practical synthertic process for a nonproteinaceous elicitor, (-)-syringolide 1, has been developed in a short number of steps utilizing the putative biosynthetic pathway by featuring the elaboration of the protected D-xylose as a starting material.
• Synthesis of syringolide 1 ketals and esters for receptor studies
  作者：Tetsu Tsurushima、Sharon L. Midland、Chun-min Zeng、Cheng Ji、James J. Sims、Noel T. Keen

  DOI：10.1016/s0031-9422(96)00530-4

  日期：1996.12

  The syringolides, specified by avirulence gene D from Pseudomonas syringae, elicit a disease defense reaction only in soybean cultivars carrying the Rpg4 disease resistance gene. In order to identify structural features important for elicitor activity and construct highly labelled elicitor-active probes, several syringolide esters and ketals were synthesized. Alteration of the C-3 hemiketal group of syringolide 1 abolished elicitor activity, but ester derivatives based on the C-4' hydroxy group all retained activity. [I-125]4'-(2-iodo-3,4,5-trimethoxyphenylacetyl) syringolide 1 was prepared for receptor studies. Copyright (C) 1996 Elsevier Science Ltd
• 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。
• 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.