(R)-3-<(p-Toluenesulfonyl)oxy>thiolane 1(R)-oxide | 120788-02-5

• 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: (R)-3-<(p-Toluenesulfonyl)oxy>thiolane 1(R)-oxide
• 英文别名: 3R-(p-Toluenesulfonyloxy)thiolane 1R-Oxide；(R)-3-[(p-Toluenesulfonyl)oxy]thiolane 1(R)-oxide；[(1R,3R)-1-oxothiolan-3-yl] 4-methylbenzenesulfonate
• CAS: 120788-02-5
• 化学式: C₁₁H₁₄O₄S₂
• 分子量: 274.362
• InChiKey: KSPRQIQTVLZCLF-QLJPJBMISA-N

物化性质

• 沸点：
  510.8±39.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  88
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-<(p-Toluenesulfonyl)oxy>thiolane 1(R)-oxide 、 potassium thioacetate 以 丙酮 为溶剂， 以80%的产率得到(S)-3-(Acetylthio)thiolane 1(R)-oxide
  参考文献：
  名称：

  硫培南侧链的合成方法

  摘要：

  本发明公开了一种硫培南侧链的合成方法。该合成方法包括以下步骤：以为原料采用酮还原酶还原生成进而通过单加氧酶氧化生成对进行对甲苯磺酰基保护后，再通过硫酰基保护得到目标产物应用本发明的技术方案，使用酮还原酶和单加氧酶，分别进行第一步和第二步两步生物转化，再将第二步氧化产物进行Ts(对甲苯磺酰基)保护后，最后通过硫酰基保护得到目标产物，由于第一步和第二步均为生物转化，不需要通过乙酸乙酯萃取，减少了乙酸乙酯的用量。

  公开号：

  CN109796434B
• 作为产物：
  描述：

  (R)-1,2-bis<(p-tolylsulfonyl)oxy>-4-(methylthio)butane 在 吡啶 、 peracid 、 三氟乙酸 作用下， 以 苯 为溶剂， 生成 (R)-3-<(p-Toluenesulfonyl)oxy>thiolane 1(R)-oxide
  参考文献：
  名称：

  Synthesis of optically active 3(R)-[(alkylsulfonyl)oxy]thiolanes from 2(R)-hydroxy-4-(methylthio)butanoic acid or D-methionine

  摘要：

  DOI：

  10.1021/jo00298a057

文献信息

• 2-Alkylthiopenem derivatives
  申请人：PFIZER INC.

  公开号：EP0130025A1

  公开（公告）日：1985-01-02

  2-alkylthio-2-penem-3- carboxylic acid compounds, useful as antibacterials for treating mammals, have the formula: or a pharmaceutically acceptable salt thereof, wherein: R is 2-(methylsulfinyl) ethyl, 2-(methylsulfonyl)- ethyl, (methylsulfinyl)methyl, (methylsulfonyl)methyl, 3-thietanyl, 1-oxo-3-thietanyl, 1,1-dioxo-3-thietanyl, 2-thiolanyl, 1-oxo-2-thiolanyl, 3-thiolanyl, 1-oxo-3-thiolanyl, 1,1-dioxo-3-thiolanyl, 3-hydroxy-4-thiolanyl, 1-oxo-3-hydroxy-thiolanyl, 1, 1-dioxo-3-hydroxy-4-thiolanyl, 2-oxo-1, 3-dithiolan, 4-ylmethyl, 3-thianyl, 1-oxo-3-thianyl, 1, 1-dioxo-3-thianyl, 4-thianyl, 1-oxo-4-thianyl, 1, 1-dioxo-4-thianyl, 3-oxo-perhydro-1, 4-thiazin-2-yl. 4-formylperhydro-1, 4-thiazin-2-yl, 4-oxo-1, 4-oxathian-3-yl, 4, 4-dioxo-1, 4-oxathian-3-yl, 1, 3-dithiolan-2-yl, 1, 2-dithiolan-4-yl, or (2-methyl-3, 3-dioxo-1, 3-oxathiolan-5-yl) methyl; and R, is hydrogen or a group which forms an ester which is hydrolyzed in vivo.

  作为治疗哺乳动物的抗菌剂的 2-烷硫基-2-烯-3-羧酸化合物具有以下式子： 或其药学上可接受的盐，其中 R是 2-(甲磺酰)乙基、2-(甲磺酰)-乙基、(甲磺酰)甲基、(甲磺酰)甲基、3-硫杂环丁烷、1-氧代-3-硫杂环丁烷、1,1-二氧代-3-硫杂环丁烷、2-硫杂环丁烷、1-氧代-2-硫杂环丁烷、3-硫杂环丁烷、1-氧代-3-硫杂环丁烷、1,1-二氧代-3-硫杂环丁烷、3-hydroxy-4-thiolanyl, 1-oxo-3-hydroxy-thiolanyl, 1, 1-dioxo-3-hydroxy-4-thiolanyl, 2-oxo-1, 3-dithiolan, 4-ylmethyl, 3-thianyl, 1-oxo-3-thianyl, 1, 1-dioxo-3-thianyl, 4-thianyl, 1-oxo-4-thianyl, 1, 1-dioxo-4-thianyl, 3-oxo perhydro-1, 4-thiazin-2-yl.4-甲酰过氢-1，4-噻嗪-2-基，4-氧代-1，4-氧硫杂环戊-3-基，4，4-二氧代-1，4-氧硫杂环戊-3-基，1，3-二硫环戊-2-基，1，2-二硫环戊-4-基，或（2-甲基-3，3-二氧代-1，3-氧硫杂环戊-5-基）甲基；以及 R，是氢或可形成在体内水解的酯的基团。
• 2-Thioalkyl penems: an efficient synthesis of sulopenem, a (5R,6S)-6-(1(R)-hydroxyethyl)-2-[(cis-1-oxo-3-thiolanyl)thio]-2-penem antibacterial
  作者：Robert A. Volkmann、Paul R. Kelbaugh、Deane M. Nason、V. John Jasys

  DOI：10.1021/jo00042a010

  日期：1992.7

  A practical synthesis of potent penem antibacterials, CP-70,429 (1) (sulopenem) and CP-81,054 (2), is described. (L)-Aspartic acid was utilized to generate both the (3S)- and (3R)-thiolanylthio side chains of (5R,6S)-6-(1-(R)-hydroxyethyl)-2-[(cis-1-oxo-3-thiolanyl)thio]-2-penem-3-carboxylic acids 1 and 2. This synthetic pathway provided in high yield enantiopure thioacetate intermediates 15 and 19. To accommodate the fragile side chain sulfoxide moiety of the targeted beta-lactams, standard penem synthetic methodology was modified to facilitate the conversion of 15 and 19 to 1 and 2. The reactive chloroazetidinone 4b was utilized to generate key azetidinone trithiocarbonate intermediate 22 which contains the requisite penem side chain. A chemoselective oxalofluoride-based azetidinone N-acylation procedure, which avoids sulfoxide O-acylation, was required for the conversion of 22 to the penem framework.
• VOLKMANN, ROBERT A.
  作者：VOLKMANN, ROBERT A.

  DOI：——

  日期：——
• IMPROVED KETOREDUCTASE POLYPEPTIDES FOR THE STEREOSELECTIVE PRODUCTION OF (R)-3-HYDROXYTHIOLANE
  申请人：Codexis, Inc.

  公开号：EP2195443B1

  公开（公告）日：2015-01-07
• Ketoreductase Polypeptides for the Production of (R)-3-Hydroxythiolane
  申请人：Liang Jack

  公开号：US20090093031A1

  公开（公告）日：2009-04-09

  The present disclosure provides engineered ketoreductase enzymes having improved properties as compared to a naturally occurring wild-type ketoreductase enzyme. Also provided are polynucleotides encoding the engineered ketoreductase enzymes, host cells capable of expressing the engineered ketoreductase enzymes, and methods of using the engineered ketoreductase enzymes to synthesize chiral compounds.