(1'R,2'R)-3-[1'-hydroxy-2',3'-(isopropylidenedioxy)propyl]but-2-en-4-olide | 184780-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'R,2'R)-3-[1'-hydroxy-2',3'-(isopropylidenedioxy)propyl]but-2-en-4-olide
• 英文别名: 3-[(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2H-furan-5-one
• CAS: 184780-72-1
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: BPAZNBYONXOXTM-VXNVDRBHSA-N

物化性质

• 沸点：
  402.7±30.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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-hydroxyoctyl)-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
• 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 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+

文献信息

• Synthesis of the Syributins and Formal Total Synthesis of Syringolide 1.
  作者：Romina Di Florio、Mark A. Rizzacasa

  DOI：10.1071/ch99170

  日期：——

  A synthesis of syributins 1 (5) and 2 (6) from D-glyceraldehyde acetonide (12)and furans (14) and (15) is described. Compounds (5) and (6) are cometabolitesof the novel non-proteinaceous C-glycosidic elicitormolecules the syringolides 1 (1) and 2 (2). Under a variety of acidicconditions, the intermediate butenolides (9) and (10) provided syributins 1(5) and 2 (6). Similar results have been reported

  描述了由 D-甘油醛丙酮化物 (12) 和呋喃 (14) 和 (15) 合成 syributins 1 (5) 和 2 (6)。化合物 (5) 和 (6) 是新的非蛋白质 C-糖苷诱导分子丁香内酯 1 (1) 和 2 (2) 的代谢物。在各种酸性条件下，中间体丁烯内酯 (9) 和 (10) 提供了 syributins 1(5) 和 2 (6)。Honda 和同事报告了类似的结果，他们将丁烯内酯 (20) 转化为丁香内酯 1 (1)。由于化合物(20)也是通过本新路线合成的，因此已经实现了丁香内酯1(1)的正式合成。
• Use of a Baylis–Hillman adduct in the stereoselective synthesis of syributins via a RCM protocol
  作者：Palakodety Radha Krishna、M. Narsingam、V. Kannan

  DOI：10.1016/j.tetlet.2004.04.080

  日期：2004.6

  The total synthesis of syributins 1 and 2 using the Baylis–Hillman adduct of 2,3-O-isopropylidene-R-glyceraldehyde-ethyl acrylate as starting material followed by ring closing metathesis (RCM) of the acrylate derivative of the ensuing diol as the key step is reported.

  syributins的全合成1和2使用2,3-的的Baylis-希尔曼加合物ö异亚丙基- [R甘油醛-丙烯酸乙酯作为起始材料，随后通过随后的二醇作为的丙烯酸酯衍生物的闭环复分解（RCM）报告了关键步骤。
• Total Syntheses of (+)-Secosyrins 1 and 2 and (+)-Syributins 1 and 2
  作者：Chisato Mukai、Sameh M. Moharram、Satoru Azukizawa、Miyoji Hanaoka

  DOI：10.1021/jo9711089

  日期：1997.11.1

  First total syntheses of (+)-secosyrins 1 and 2 and total syntheses of (+)-syributins 1 and 2 are described. The two chiral centers of diisopropyl tartrate were incorporated into target natural products. Stereoselective construction of the spiro skeleton of secosyrins could be realized by taking advantage of an alkyne-cobalt complex. The synthesis of these compounds established their relative and absolute

  首先描述（+）-丝球菌素1和2的总合成，以及（+）-丝氨酸酪蛋白1和2的总合成。将酒石酸二异丙酯的两个手性中心并入目标天然产物中。可以通过利用炔-钴配合物来实现立体定位的椰油香豆素螺旋骨架的立体选择性构建。这些化合物的合成明确地建立了它们的相对和绝对立体化学。
• 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.
• Total Syntheses of Sphydrofuran, Secosyrins, and Syributins^,¹
  作者：Pei Yu、Yun Yang、Ze Ying Zhang、Thomas C. W. Mak、Henry N. C. Wong

  DOI：10.1021/jo970476+

  日期：1997.9.1

  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.