methyl (3R,4S,5R)-3-[(tert-butyldimethylsilyl)oxy]-4,5-(2,3-dimethoxybutan-2,3-dioxy)cyclohex-1-ene-1-carboxylate | 433693-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3R,4S,5R)-3-[(tert-butyldimethylsilyl)oxy]-4,5-(2,3-dimethoxybutan-2,3-dioxy)cyclohex-1-ene-1-carboxylate
• 英文别名: methyl (3R,4S,5R)-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutan-2,3-dioxy)-cyclohex-1-ene-1-carboxylate；(2'S,3'S)-methyl 3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)shikimate；methyl (2S,3S,4aS,5R,8aR)-5-[tert-butyl(dimethyl)silyl]oxy-2,3-dimethoxy-2,3-dimethyl-4a,5,8,8a-tetrahydro-1,4-benzodioxine-7-carboxylate
• CAS: 433693-06-2
• 化学式: C₂₀H₃₆O₇Si
• 分子量: 416.587
• InChiKey: BJQVMUFQJXEVCI-ZGMAETJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (3R,4S,5R)-3-[(tert-butyldimethylsilyl)oxy]-4,5-(2,3-dimethoxybutan-2,3-dioxy)cyclohex-1-ene-1-carboxylate 在 三氟乙酸 作用下， 生成 methyl shikimate
  参考文献：
  名称：

  Dehydration of Quinate Derivatives: Synthesis of a Difluoromethylene Homologue of Shikimic Acid

  摘要：

  我们利用马丁硫醚 {Ph2S[OC(CF3)2Ph]2} 开发出了一种将醌酯结构转化为莽草酸结构的优化程序。在合成莽草酸的新型二氟亚甲基同系物时利用了这一程序。

  DOI：

  10.1055/s-2002-19772
• 作为产物：
  描述：

  (2'S,3'S)-methyl 3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate 在 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以84%的产率得到methyl (3R,4S,5R)-3-[(tert-butyldimethylsilyl)oxy]-4,5-(2,3-dimethoxybutan-2,3-dioxy)cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  Difluorinated analogues of shikimic acid

  摘要：

  Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00697-5

文献信息

• A Lemieux–Johnson oxidation of shikimic acid derivatives: facile entry to small library of protected (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals
  作者：Miroslav Psotka、Miroslava Martinková、Jozef Gonda

  DOI：10.1007/s11696-016-0004-8

  日期：2017.4

  The Lemieux–Johnson oxidation was employed for the cleavage of the carbon–carbon double bond of shikimic acid derivatives. Through this procedure, a series of the sixteen novel (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals bearing three contiguous stereocentres have been synthesized in excellent yields.

  Lemieux-Johnson氧化法用于裂解iki草酸衍生物的碳-碳双键。通过该程序，已经以优异的产率合成了一系列具有三个连续立体中心的十六种新颖的（2 S，3 S，4 R）-2,3,4,7-四羟基-6-氧庚烷。
• A-Ring-Modified 2-Hydroxyethylidene Previtamin D₃Analogues: Synthesis and Biological Evaluation
  作者：Alba Hernández-Martín、Susana Fernández、Annemieke Verstuyf、Lieve Verlinden、Miguel Ferrero

  DOI：10.1002/ejoc.201601263

  日期：2017.1.18

  To investigate the biological profile of the previtamin form of vitamin D, we synthesized new analogues of 19-nor-1α,25-dihydroxyprevitamin D3 bearing a 2-hydroxyethylidene moiety at the A-ring. The target compounds were prepared by convergent synthesis using a Sonogashira coupling between an A-ring enyne synthon and a CD-ring/side-chain vinyl triflate. We have demonstrated the versatility of shikimic

  为了研究维生素 D 前维生素形式的生物学特征，我们合成了在 A 环上带有 2-羟基亚乙基部分的 19-nor-1α,25-二羟基前维生素 D3 的新类似物。使用 A 环烯炔合成子和 CD 环/侧链乙烯基三氟甲磺酸酯之间的 Sonogashira 偶联，通过会聚合成制备目标化合物。我们已经证明了莽草酸作为合成 A 环前体的起始材料的多功能性。评估了对维生素 D 受体 (VDR) 和人类维生素 D 结合蛋白 (hDBP) 的结合亲和力，以及 MCF-7 细胞的抗增殖活性。
• A Suzuki Cross-Coupling and Intramolecular Aza-Michael Addition Reaction Sequence Towards the Synthesis of 1,10b-<i>epi</i>-7-Deoxypancratistatins and Their Cytotoxicity Studies
  作者：Ganesh Pandey、Madhesan Balakrishnan、Pandrangi Siva Swaroop

  DOI：10.1002/ejoc.200800830

  日期：2008.12

  phenanthridone is described. The convergent strategy commences with the preparation of Suzuki cross-coupling reaction precursors, arylboronic acid 12 and α-iodo enone 19, from piperonylamine (9) and (–)-D-quinic acid (10), respectively. The coupling of 12 and 19 followed by a key intramolecular aza-Michael addition produced phenanthridone 21 featuring a cis-fused B–C ring junction. The syntheses of compounds 25

  描述了构建菲啶酮的有效方法的开发。收敛策略从分别从胡椒胺 (9) 和 (-)-D-奎尼酸 (10) 制备 Suzuki 交叉偶联反应前体、芳基硼酸 12 和 α-碘烯酮 19 开始。12 和 19 的偶联以及关键的分子内氮杂-迈克尔加成产生了具有顺式融合 B-C 环连接的菲啶酮 21。本文详细阐述了化合物 25 和 26 的合成，这两种化合物都是天然存在的强效抗肿瘤剂 7-脱氧潘克拉他汀 (2) 的 C-1 和 C-10b 差向异构体。针对三种不同的癌细胞系评估了 25 和 26 的细胞毒性。化合物 26 作为 THP-1 单核细胞的中度生长抑制剂 (GI50 = 14.5 μg/mL)。
• Synthesis of (+)-zeylenone from shikimic acid
  作者：An Liu、Zhan Zhu Liu、Zhong Mei Zou、Shi Zhi Chen、Li Zhen Xu、Shi Lin Yang

  DOI：10.1016/j.tet.2004.02.066

  日期：2004.4

  Starting from shikimic acid, the total synthesis of zeylenone was studied. The product was proved to be the (+)antipode of zeylenone through analysis and comparison of their respective spectra (including NMR, MS, IR and CD) and optical data. The absolute configuration of the natural product was thus determined to be (1S,2S,3R).

  从sh草酸开始，研究了玉米y酮的全合成。通过分析和比较其各自的光谱（包括NMR，MS，IR和CD）和光学数据，证明该产物是玉米烯酮的（+）ode。因此确定天然产物的绝对构型为（1 S，2 S，3 R）。
• 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。