(4S,5R)-methyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate | 28762-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-methyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• 英文别名: (2S,3R)-methyl 5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylate；methyl [(2S,3R)-4-hydroxy-2,3-(isopropylidenedioxy)]butan-1-oate；methyl 2,3-O-isopropylidene-D-threonate；methyl (4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 28762-00-7
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: JMYFRHOMDFXPSE-RITPCOANSA-N

物化性质

• 沸点：
  244.0±25.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (4S,5R)-methyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 在 sodium azide 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成 (4S,5R)-isopropyl 5-(azidomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
  参考文献：
  名称：

  Bend-ribbon forming γ-peptides

  摘要：

  骨架受五元环约束的同手性和异手性四元δ肽衍生物在溶液中形成了弯曲带构象，并通过分子内氢键得以稳定。

  DOI：

  10.1039/b706528k
• 作为产物：
  描述：

  methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butyrate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以82%的产率得到(4S,5R)-methyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
  参考文献：
  名称：

  使用2,2-二甲基-1,3-二氧戊环-4-甲醇及其相关化合物作为受体，与6'-氯-6'-脱氧蔗糖和固定化的异麦芽酮糖微生物进行转葡糖基化反应。葡糖基受体的立体和化学要求。

  摘要：

  使用三种固定化的异麦芽酮糖生产微生物，在合成供体的转葡萄糖基化反应中观察到了2,3-O-异亚丙基-赤藓糖醇的对映选择性和非对映选择性α-D-葡萄糖基化。取决于所使用的微生物，还以中等或良好的收率将包括2,3-O-异亚丙基亚乙基玫瑰二甲基二硫缩醛和醛糖醛酸酯的一些相关化合物进行糖基化。关于葡糖基受体的底物特异性，讨论了立体和官能团因素。

  DOI：

  10.1016/s0008-6215(05)80009-6

文献信息

• Stereoselective Total Syntheses of Uncommon Sesquiterpenoids Isolated from <i>Jatropha neopauciflora</i>
  作者：Yujiro Hayashi、Naoki Miyakoshi、Shinji Kitagaki、Chisato Mukai

  DOI：10.1021/ol800633a

  日期：2008.6.1

  neopauciflora, were completed from dimethyl D-tartrate in a stereoselective manner. The crucial steps in these syntheses involved not only the Rh(I)-catalyzed Pauson-Khand-type reaction of the allenene derivative leading to the exclusive formation of the bicyclo[4.3.0]nonenone framework possessing an angular methyl group but also a highly stereoselective construction of the isopropylcyclopropane ring.

  从新麻风树属麻风树中分离的两个三环倍半萜烯1和2的第一批总合成是从D-酒石酸二甲酯以立体选择性的方式完成的。这些合成过程中的关键步骤不仅涉及艾伦烯衍生物的Rh（I）催化的Pauson-Khand型反应，导致排他性地形成具有角甲基的双环[4.3.0]壬烯酮骨架，而且还涉及异丙基环丙烷环的立体选择性结构。
• AMINOGLYCOSIDE DERIVATIVES
  申请人：Glinka Tomasz W.

  公开号：US20130059808A1

  公开（公告）日：2013-03-07

  The present invention relates to antimicrobial agents. Some embodiments include compounds, compositions, methods of preparation, and methods of treatment using new aminoglycosides and aminoglycoside derivatives.

  本发明涉及抗微生物剂。一些实施例包括新的氨基糖苷和氨基糖苷衍生物的化合物、组合物、制备方法和治疗方法。
• Total Synthesis and Functional Evaluation of IORs, Sulfonolipid‐based Inhibitors of Cell Differentiation in <i>Salpingoeca rosetta</i>
  作者：Luka Raguž、Chia‐Chi Peng、Florentine U. N. Rutaganira、Thomas Krüger、Aleksa Stanišić、Theresa Jautzus、Hajo Kries、Olaf Kniemeyer、Axel A. Brakhage、Nicole King、Christine Beemelmanns

  DOI：10.1002/anie.202209105

  日期：2022.10.10

  modular synthesis of the rosette-inhibitor sulfonolipid IOR-1A and chemical probes was achieved via decarboxylative cross-coupling reaction of a desymmetrized tartaric acid derivatives and alkyl zinc reagents of choice. Synthesized congeners and bifunctional probes allowed to determine structure-activity relation to profile binding partners in producer and recipient for the first time.

  通过脱对称酒石酸衍生物和所选烷基锌试剂的脱羧交叉偶联反应，实现了玫瑰花结抑制剂磺脂 IOR-1A 和化学探针的新型模块化合成。合成的同类物和双功能探针首次允许确定生产者和接受者中配置文件绑定伙伴的结构-活动关系。
• Asymmetric Total Synthesis of the 1-<i>e</i><i>pi</i>-Aglycon of the Cripowellins A and B
  作者：Dieter Enders、Achim Lenzen、Michael Backes、Carsten Janeck、Kelly Catlin、Marie-Isabelle Lannou、Jan Runsink、Gerhard Raabe

  DOI：10.1021/jo0518093

  日期：2005.12.1

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.
• Synthesis and Evaluation of 1-Deoxy-<scp>d</scp>-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase
  作者：Joel R. Walker、C. Dale Poulter

  DOI：10.1021/jo0516786

  日期：2005.11.1

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.