(S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one p-toluenesulfonate | 174563-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one p-toluenesulfonate
• 英文别名: toluene-4-sulfonic acid 2-((4S)-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)ethyl ester；2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]ethyl 4-methylbenzenesulfonate；(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-YL)ethyl 4-methylbenzenesulfonate
• CAS: 174563-84-9
• 化学式: C₁₄H₁₈O₆S
• 分子量: 314.359
• InChiKey: ZACOOYYGQAUYSK-LBPRGKRZSA-N

物化性质

• 沸点：
  461.2±25.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one p-toluenesulfonate 在 正丁基锂 、 碘化亚铜 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 以2.44 g (95%)的产率得到(S)-5-Hexyl-2,2-dimethyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  Optically pure 4-alkenyl- or 4-alkanyl-2-hydroxytetronic acids and

  摘要：

  本发明涉及一种从光学纯醛合成光学纯的4-烯基或4-烷基-2-羟基四酮酸的方法。该发明还涉及将这些光学纯化合物作为有效的血小板聚集抑制剂，通过在环氧化酶水平上发挥作用。此外，该发明还涉及将这些化合物在治疗冠状动脉疾病中的药用，特别是在动脉粥样硬化的治疗和/或预防中的药用。

  公开号：

  US05504107A1
• 作为产物：
  描述：

  (S)-[2,2-二甲基-5-氧代二氧戊环-4-基]乙酸 在 吡啶 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one p-toluenesulfonate
  参考文献：
  名称：

  新型金属蛋白酶抑制剂的设计与合成。

  摘要：

  合成了一系列的N-苯甲酰基4-氨基丁酸异羟肟酸酯类似物，并将其评估为基质金属蛋白酶抑制剂。合成工作的重点是使用容易获得的起始原料对4-氨基丁酸部分进行化学修饰。这样，使用可商购的起始原料例如4-氨基丁酸，（+）-和（-）-苹果酸以及D-和L-谷氨酸衍生物进行化学修饰。在测试的化合物中，衍生自L-谷氨酸的N- [4-（苯并呋喃-2-基）苯甲酰基] 4-氨基-4S-羟甲基丁酸异羟肟酸酯与MMP-2和MMP-9相比，对MMP-2和MMP-9的抑制作用更强。分别衍生自（-）-苹果酸的相应2S-羟基类似物或3S-羟基类似物。提出了构效关系研究。

  DOI：

  10.1016/j.bmc.2006.03.032

文献信息

• Synthesis of optically pure 4-alkenyl- or 4-alkanyl-2-hydroxytetronic
  申请人：The Ohio State University Research Foundation

  公开号：US05656662A1

  公开（公告）日：1997-08-12

  The present invention relates to a method for synthesis of optically pure 4-alkenyl or 4-alkanyl-2-hydroxytetronic acids from an optically pure aldehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase, thus making them useful in the treatment of coronary artery diseases, especially atherosclerosis, and additionally, as inhibitors of various inflammatory cytokines, making them useful in the treatment of both acute and chronic inflammation, as well in the treatment of cachexia, rheumatoid arthritis, multiple sclerosis, Crohn's disease and ulcerative colitis. The invention further relates to pharmaceutical compositions of the instant compounds.

  本发明涉及一种从光学纯醛合成光学纯4-烯基或4-烷基-2-羟基四氢呋喃酸的方法。本发明还涉及将这些光学纯化合物作为强效的血小板聚集抑制剂，通过作用于环氧合酶水平，从而使它们在治疗冠状动脉疾病，特别是动脉粥样硬化方面有用，并且作为各种炎症细胞因子的抑制剂，使其在急性和慢性炎症治疗，以及消耗症、类风湿性关节炎、多发性硬化症、克罗恩病和溃疡性结肠炎治疗中有用。本发明还涉及这些化合物的制药组合物。
• A METHOD FOR PREPARING 4-Ý9-(6-AMINOPURINE)¨-2-(S)-HYDROXYL-BUTYRIC ACID METHYL ESTER
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：EP2230239A1

  公开（公告）日：2010-09-22

  The present invention discloses a novel method for preparing and purifying 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester. The preparation started from cheap and easily available L-malic acid, which was transformed to intermediate I after simultaneous protection of the groups of 1-carboxyl and 2-hydroxyl. The intermediate I was selectively reduced to intermediate alcohol II, whose hydroxyl group was further transformed to an easily leaving group to afford intermediate III. The intermediate III was nucleophilically substituted with adenine to afford intermediate IV The intermediate IV was deprotected and methyl-esterified simultaneously in methanol in the presence of an acid or a base to afford crude 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester, which was purified by recrystallization to afford the purified product. Comparing with the prior preparation methods, the present method has advantages in low cost, mild conditions, high retention of the chiral center during the reaction, high productivity, great improvement in the quality and yield of the product and great decrease in cost, and thus is suitable for the production on a large scale.

  本发明公开了一种制备和纯化 4-(6-氨基-嘌呤-9-基)-2(S)-羟基丁酸甲酯的新方法。该制备方法从廉价易得的 L-苹果酸开始，在同时保护 1-羧基和 2-羟基后将其转化为中间体 I。中间体 I 被选择性地还原成中间体醇 II，其羟基进一步转化为易离去基团，得到中间体 III。中间体 IV 在甲醇中，在酸或碱的存在下同时进行脱保护和甲基酯化，得到粗制的 4-(6-氨基-嘌呤-9-基)-2(S)-羟基丁酸甲酯。与之前的制备方法相比，本方法具有成本低、条件温和、反应过程中手性中心保留率高、生产率高、产品质量和收率大大提高、成本大大降低等优点，适合大规模生产。
• Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers
  作者：Yang-Ming Zhang、Yu Ding、Wei Tang、Wei Luo、Min Gu、Wei Lu、Jie Tang、Jian-Ping Zuo、Fa-Jun Nan

  DOI：10.1016/j.bmc.2008.09.017

  日期：2008.10

  DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respective inhibitory potency of SAHase, the immunosuppressive potency order was demonstrated as (S)-Z2002 > (Rac)-DZ2002 > (R)-DZ2002 > (Keto)DZ2002. These results indicate (S)-configuration of 2-chiral center in DZ2002 is important for binding with SAHase. (C) 2008 Elsevier Ltd. All rights reserved.
• EP2230239
  申请人：——

  公开号：——

  公开（公告）日：——
• Method for Preparing 4-[9-(6-Aminopurine)]-2-(S)-Hydroxyl-Butyric Acid Methyl Ester
  申请人：Nan Fajun

  公开号：US20110201810A1

  公开（公告）日：2011-08-18

  The present invention discloses a novel method for preparing and purifying 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester. The preparation started from cheap and easily available L-malic acid, which was transformed to intermediate I after simultaneous protection of the groups of 1-carboxyl and 2-hydroxyl. The intermediate I was selectively reduced to intermediate alcohol II, whose hydroxyl group was further transformed to an easily leaving group to afford intermediate III. The intermediate III was nucleophilically substituted with adenine to afford intermediate IV. The intermediate IV was deprotected and methyl-esterified simultaneously in methanol in the presence of an acid or a base to afford crude 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester, which was purified by recrystallization to afford the purified product. Comparing with the prior preparation methods, the present method has advantages in low cost, mild conditions, high retention of the chiral center during the reaction, high productivity, great improvement in the quality and yield of the product and great decrease in cost, and thus is suitable for the production on a large scale.