(S)-5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxolan-4-one | 193538-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxolan-4-one
• 英文别名: (5S)-5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxolan-4-one
• CAS: 193538-54-4
• 化学式: C₇H₁₁BrO₃
• 分子量: 223.067
• InChiKey: OUQKGLRPEIEHJI-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-methylbutyl)prop-2-en-1-ol 、 (S)-5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxolan-4-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 6.0h， 以80%的产率得到(S)-4-Bromo-2-hydroxy-butyric acid 5-methyl-2-methylene-hexyl ester
  参考文献：
  名称：

  天然 (+)-Lasonolide A 的立体选择性全合成

  摘要：

  天然 (+)-lasonolide A (1) 是一种抗肿瘤剂，通过在 C 2 2 四元手性中心形成热力学亚苄基，使用二砜当量延长 C 1 5 -C 1 7 合成三碳链以及在C 1 5 和C 1 7 处引入两个反式烯烃，上层THP的碘环化。底部 THP 的 Michael 加成和 20 元大环内酯的分子内 Horner-Emmons 烯化。

  DOI：

  10.1055/s-2004-822340
• 作为产物：
  描述：

  (S)-5-(2-羟基乙基)-2,2-二甲基-1,3-二噁烷-4-酮 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(S)-5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  苹果酸：合成肽二级结构模拟物的便利前体

  摘要：

  描述了经由衍生自（S）-或（R）-苹果酸的4-溴-2-羟基丁酸酯通过光学活性醚连接的β-内酰胺和氮杂脯氨酸类似物的合成。从这些中间体可以合成肽二级结构模拟物。

  DOI：

  10.1016/s0040-4039(97)01083-6

文献信息

• [EN] ARYLOXYACETYLINDOLES AND ANALOGS AS ANTIBIOTIC TOLERANCE INHIBITORS<br/>[FR] ARYLOXYACÉTYLINDOLES ET ANALOGUES EN TANT QU'INHIBITEURS DE TOLÉRANCE AUX ANTIBIOTIQUES
  申请人：SPERO THERAPEUTICS INC

  公开号：WO2016112088A1

  公开（公告）日：2016-07-14

  The disclosure provides compounds and pharmaceutical compositions of aryloxyacetylindoles compounds and analogs useful for treating chronic and acute bacterial infections. Certain of the compounds are compounds of general Formula (I) (I) or a pharmaceutically acceptable salt or prodrug thereof. Certain compounds of this disclosure are MvfR inhibitors. MvfR inhibitors reduce the formation of antibiotic tolerant bacterial strains and are useful for treating Gram-negative bacterial infections and reducing the virulence of Pseudomonas aeruginosa. Methods of treating bacterial infections in a subject, including Pseudomonas aeruginosa infections, are also provided by the disclosure.

  该披露提供了芳基氧乙酰基吲哚化合物及类似物的化合物和药物组合物，用于治疗慢性和急性细菌感染。其中某些化合物是一般式(I)（I）的化合物或其药用可接受的盐或前药。该披露的某些化合物是MvfR抑制剂。MvfR抑制剂减少抗生素耐药细菌菌株的形成，对治疗革兰氏阴性细菌感染和减少铜绿假单胞菌的毒力有用。该披露还提供了治疗受试者细菌感染的方法，包括铜绿假单胞菌感染。
• 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。
• EP2230239
  申请人：——

  公开号：——

  公开（公告）日：——
• Total Synthesis of Natural (+)-Lasonolide A
  作者：Sung Ho Kang、Suk Youn Kang、Chul Min Kim、Hyeong-wook Choi、Hyuk-Sang Jun、Byeong Moon Lee、Chul Min Park、Joon Won Jeong

  DOI：10.1002/anie.200352016

  日期：2003.10.13
• 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.