((4R,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-methanol | 41167-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((4R,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-methanol
• 英文别名: [(4r,5s)-2,2,5-Trimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 41167-51-5
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: VWUQFWPEGNZUQV-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((4R,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-methanol 在 正丁基锂 、 草酰氯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (6R,7R)-6,7-(propane-2,2-dioxy)-5-hydroxyocta-2-en-4-lactone
  参考文献：
  名称：

  Versicolactones A and B: total synthesis and structure revision

  摘要：

  To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The H-1 and C-13 NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta-2,4-dien-4-lactone, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.120
• 作为产物：
  描述：

  (2S,3R)-4-benzyloxy-2,3-(propane-2,2-dioxy)butane 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以83.6%的产率得到((4R,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-methanol
  参考文献：
  名称：

  Versicolactones A and B: total synthesis and structure revision

  摘要：

  To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The H-1 and C-13 NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta-2,4-dien-4-lactone, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.120

文献信息

• Enzymatic enantioselective hydrolysis of 2,2-dimethyl-1,3-dioxolane-4-carboxylic esters
  作者：M. Pottie、J. Van der Eycken、M. Vandewalle、J.M. Dewanckele、H. Röper

  DOI：10.1016/s0040-4039(01)93775-x

  日期：1989.1

  2,2-Dimethyl-1,3-dioxolane-4-carboxylic acid derived chiral building blocks were prepared from substituted α,β-unsaturated acids with high enantiomeric purities by enzymatic hydrolysis of their n.butyl esters.

  2，2-二甲基-1，3-二氧戊环-4-羧酸衍生的手性结构单元是由具有高对映体纯度的取代的α，β-不饱和酸通过其正丁酯的酶促水解制备的。
• Reductive Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. Synthesis of Alditols with Potential Utility as Chiral Synthons
  作者：Cosme G. Francisco、Elisa I. León、Angeles Martín、Pilar Moreno、María S. Rodríguez、Ernesto Suárez

  DOI：10.1021/jo0156565

  日期：2001.10.1

  A series of anomeric nitrate esters and N-phthalimido glycosides of carbohydrates in furanose and pyranose forms have been synthesized in order to generate the corresponding alkoxy radicals and study the C1-C2 fragmentation reaction under reductive conditions. This reaction constitutes a two-step method for the transformation of carbohydrates into the corresponding alditols with one less carbon. Using

  合成了一系列呋喃糖和吡喃糖形式的碳水化合物的异头硝酸酯和N-邻苯二甲酰亚胺基糖苷，以生成相应的烷氧基，并研究还原条件下的C1-C2片段化反应。该反应构成了将碳水化合物转化为碳较少的相应糖醇的两步法。使用这种方法，已经制备了具有D-赤藓糖醇，D-苏糖醇，D-木糖醇和D-阿拉伯糖醇立体化学的天然产物合成的有趣的四碳和五碳构件。1,2-O-异亚丙基-β-L-苏糖（40）和1-乙酰氨基-2,4,5-三-O-乙酰基-D-阿拉伯糖醇（50）的合成也已从1,2实现：5,6-二-O-异亚丙基-β-D-呋喃葡萄糖和2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-D-吡喃葡萄糖，
• Substrate specificity and enantioselectivity of penicillinacylase catalyzed hydrolysis of phenacetyl esters of synthetically useful carbinols
  作者：Claudio Fuganti、Piero Grasselli、Stefano Servi、Ameriga Lazzarini、Paolo Casati

  DOI：10.1016/s0040-4020(01)81708-7

  日期：1988.1

  Penicillinacylase from , immoblized on Eupergit C beads catalyzes the hydrolysis in water/CH3CN 10:1, at pH 7.5 and 23° C, of a set of O-phenylacetate esters of primary carbinols. The highest enantioselectivity is observed in the case of the 2,2-dimethyl-1,3-dioxolane-4-methanols structurally related to the penicillin (1) framework. Minor modifications of this basic structure are not altering the acceptability

  固定在Eupergit C珠上的青霉素酰化酶催化在水/ CH 3 CN 10：1中在pH 7.5和23°C下水解一系列邻苯甲醇的邻苯乙酸酯。在与青霉素（1）骨架结构相关的2,2-二甲基-1,3-二氧戊环-4-甲醇中观察到最高的对映选择性。对这种基本结构的微小修饰不会改变酶的可接受性，但会显着降低水解的对映选择性，就像使用苯作为溶剂和与琼脂糖结合的酶一样。
• Enantiospecific synthesis of protected 4-deoxy-L-threose and 4-deoxy-L-erythrose via diastereoselective reduction of l-lactic acid-derived ketones
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano

  DOI：10.1039/c39860000136

  日期：——

  The title compounds were synthesized from L-lactic acid via an acylation–reduction sequence employing lithium bis-p-tolylthiomethanide as a formyl anion equivalent.

  标题化合物是使用双对甲苯基硫代甲硫醇锂作为甲酰基阴离子，通过酰化-还原序列由L-乳酸合成的。
• SODIUM CHANNEL BLOCKERS
  申请人：JOHNSON R. Michael

  公开号：US20080076782A1

  公开（公告）日：2008-03-27

  The present invention relates to sodium channel blockers. The present invention also includes a variety of methods of treatment using these inventive sodium channel blockers.

  本发明涉及钠通道阻滞剂。本发明还包括使用这些创新的钠通道阻滞剂的各种治疗方法。