methyl (4S,5R)-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohex-1-en-1-carboxylate | 245054-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4S,5R)-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohex-1-en-1-carboxylate
• 英文别名: methyl (4S,5R)-4,5-(2,3-dimethoxybutan-2,3-dioxy)-3-oxocyclohex-1-ene-1-carboxylate；methyl (2S,3S,4aS,8aR)-2,3-dimethoxy-2,3-dimethyl-5-oxo-8,8a-dihydro-4aH-1,4-benzodioxine-7-carboxylate
• CAS: 245054-30-2
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: LKZVCYXGORRPRF-RFHZTLPTSA-N

物化性质

• 沸点：
  384.7±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (4S,5R)-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohex-1-en-1-carboxylate 在 水 、 L-Selectride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.17h， 生成 methyl shikimate
  参考文献：
  名称：

  奎尼酸向sh草酸衍生物的有效转化

  摘要：

  （-）- sh草酸甲酯和（-）-3-表-shi草酸酯和3-氨基shi草酸酯衍生物的合成已经通过短而有效的途径由奎宁酸实现。

  DOI：

  10.1016/s0040-4020(99)00431-7
• 作为产物：
  描述：

  (2S,3S,4aR,6S,8R,8aR)-八氢-6,8-二羟基-2,3-二甲氧基-2,3-二甲基-1,4-苯并二氧杂环己-6-羧酸甲酯 在 4-二甲氨基吡啶 、 草酰氯 、 乙酸酐 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 methyl (4S,5R)-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohex-1-en-1-carboxylate
  参考文献：
  名称：

  奎尼酸向sh草酸衍生物的有效转化

  摘要：

  （-）- sh草酸甲酯和（-）-3-表-shi草酸酯和3-氨基shi草酸酯衍生物的合成已经通过短而有效的途径由奎宁酸实现。

  DOI：

  10.1016/s0040-4020(99)00431-7

文献信息

• Conversion of (−)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer
  作者：Martin G. Banwell、Alison J. Edwards、Michael Essers、Katrina A. Jolliffe

  DOI：10.1021/jo034689c

  日期：2003.8.1

  (-)-3-DHS (1), a compound available in large quantity through "engineering" of the shikimic acid pathway, has been converted over eight steps into the methyl ester, ent-2, of the (+)-enantiomer. Methyl (+)-shikimate (15) and its C-3 epimer (ent-5) have also been prepared by related means.

  （-）-3-DHS（1）是通过the草酸途径的“工程化”而大量获得的化合物，经八步转化为（+）-对映体的甲酯ent-2。（+）-shi草酸甲酯（15）及其C-3差向异构体（ent-5）也已通过相关方法制备。
• Synthesis of Spiro Carba-Sugars by Ring-Closing Metathesis
  作者：Concepción González-Bello、Luis Castedo、Francisco Javier Cañada

  DOI：10.1002/ejoc.200500655

  日期：2006.2

  Six conformationally restricted carba-sugars have been synthesized by ring-closing metathesis of a readily available diallyl keto derivative of (–)-quinic acid. The rich functionality of the resulting spiro ketone was exploited for the diastereoselective synthesis of various spiro carba-sugars: four of them polyhydroxylated and two aminopolyhydroxylated. The results of the testing of these compounds

  六种构象受限的碳水化合物已通过 (-)-奎尼酸的现成二烯丙基酮衍生物的闭环复分解合成。所得螺酮的丰富功能被用于各种螺卡巴糖的非对映选择性合成：其中四种多羟基化和两种氨基多羟基化。提供了针对各种市售糖苷酶（淀粉糖苷酶、α-和β-半乳糖苷酶、α-和β-葡萄糖苷酶、α-甘露糖苷酶、海藻糖酶和神经氨酸酶）的这些化合物的测试结果。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• New aspects of the Hunsdiecker–Barton halodecarboxylation—syntheses of phospha-shikimic acid and derivatives
  作者：Benoit Carbain、Peter B. Hitchcock、Hansjörg Streicher

  DOI：10.1016/j.tetlet.2010.03.044

  日期：2010.5

  We report an efficient synthetic approach to phospha-isosteres of important intermediates of the shikimic acid pathway by the application of the Hunsdiecker–Barton halodecarboxylation to cyclohexenylcarboxylic acids. As examples, phospha-shikimic acid, its 3-dehydro derivative and the respective monomethyl esters were synthesized. The approach has proven equally useful in the synthesis of isosteres

  我们报告了通过Hunsdiecker-Barton卤代羧化法对环己烯基羧酸的应用，对the草酸途径重要中间体的磷酸-等排物的有效合成方法。作为实例，合成了膦酰基shi草酸，其3-脱氢衍生物和相应的单甲酯。已证明该方法在合成抗病毒药物奥司他韦的等排物中同样有用。
• Mycobacterium tuberculosis Shikimate Kinase Inhibitors: Design and Simulation Studies of the Catalytic Turnover
  作者：Beatriz Blanco、Verónica Prado、Emilio Lence、José M. Otero、Carmela Garcia-Doval、Mark J. van Raaij、Antonio L. Llamas-Saiz、Heather Lamb、Alastair R. Hawkins、Concepción González-Bello

  DOI：10.1021/ja405853p

  日期：2013.8.21

  Shikimate kinase (SK) is an essential enzyme in several pathogenic bacteria and does not have any counterpart in human cells, thus making it an attractive target for the development of new antibiotics. The key interactions of the substrate and product binding and the enzyme movements that are essential for catalytic turnover of the Mycobacterium tuberculosis shikimate kinase enzyme (Mt-SK) have been investigated by structural and computational studies. Based on these studies several substrate analogs were designed and assayed. The crystal structure of Mt-SK in complex with ADP and one of the most potent inhibitors has been solved at 2.15 angstrom. These studies reveal that the fixation of the diaxial conformation of the C4 and C5 hydroxyl groups recognized by the enzyme or the replacement of the C3 hydroxyl group in the natural substrate by an amino group is a promising strategy for inhibition because it causes a dramatic reduction of the flexibility of the LID and shikimic acid binding domains. Molecular dynamics simulation studies showed that the product is expelled from the active site by three arginines (Arg117, Arg136, and Arg58). This finding represents a previously unknown key role of these conserved residues. These studies highlight the key role of the shikimic acid binding domain in the catalysis and provide guidance for future inhibitor designs.
• Synthesis of 3-deoxy-3,3-difluoroshikimic acid and its 4-epimer from quinic acid
  作者：Shende Jiang、Gurdial Singh、Deborah J Boam、John R Coggins

  DOI：10.1016/s0957-4166(99)00447-4

  日期：1999.10

  3-Deoxy-3,3-difluoroshikimic acid 2 and its 4-epimer 3 as new analogues of shikimic acid have been synthesised from quinic acid in overall yields of 30% and 12%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.