(2S,4R)-4-Acetylsulfanyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester | 477293-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,4R)-4-Acetylsulfanyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: 1,1-Dimethylethyl (2S,4R)-4-(acetylthio)-2-methyl-1-pyrrolidinecarboxylate；tert-butyl (2S,4R)-4-acetylsulfanyl-2-methylpyrrolidine-1-carboxylate
• CAS: 477293-61-1
• 化学式: C₁₂H₂₁NO₃S
• 分子量: 259.37
• InChiKey: MHXHTGROIMYFHU-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-Acetylsulfanyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester 在 sodium methylate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 prop-2-enyl (1S,2S,4R,5R,8R,9S,11R)-9-formyl-5-methyl-2-[[(3R,5S)-5-methylpyrrolidin-3-yl]sulfanylmethyl]-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of novel pyrrolidinyl sordaricin derivatives as antifungal agents

  摘要：

  N-Benzyl pyrrolidinyl sordaricin derivatives have been synthesized from cis-4-hydroxy-D-proline in a stereocontrolled manner. These compounds maintained moderate antifungal activity against several pathogenic fungal strains. Their MIC values against Candida albicans were in the range of 0.25-2 mug/mL. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00534-6
• 作为产物：
  描述：

  (2S,4R)-4-羟基-2-甲基-吡咯烷-1-甲酸叔丁酯 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,4R)-4-Acetylsulfanyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and evaluation of novel pyrrolidinyl sordaricin derivatives as antifungal agents

  摘要：

  N-Benzyl pyrrolidinyl sordaricin derivatives have been synthesized from cis-4-hydroxy-D-proline in a stereocontrolled manner. These compounds maintained moderate antifungal activity against several pathogenic fungal strains. Their MIC values against Candida albicans were in the range of 0.25-2 mug/mL. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00534-6

文献信息

• A production method for sulfamide
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD.

  公开号：EP0557122A1

  公开（公告）日：1993-08-25

  The method for producing a sulfamide according to the present invention includes the step of reacting an alcohol and an oxycarbonylsulfamide compound in the presence of a trivalent phosphorus compound and an azodicarboxylic acid derivative. In one embodiment, the sulfamide is represented by Formula I, the alcohol is represented by Formula II, and the oxycarbonylsulfamide compound is represented by Formula III:         R³NHSO₂NR¹R²   (I) wherein R¹ and R² are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl, a heterocyclic group, and alkyl substituted with the heterocyclic group, respectively, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, an azetidinone ring, a cephem ring, a penem ring, and a carbapenem ring; R³ is selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, a heterocyclic group, alkyl substituted with the heterocyclic group, and pyrrolidinyl-methyl, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, an azetidinone ring, a cephem ring, a penem ring, and a carbapenem ring;         R³OH   (II) wherein R³ is defined as above;         R⁴OOC-NHSO₂NR¹R²   (III) wherein R¹ and R² are defined as above; and R⁴ is a carboxy protecting group.

  根据本发明生产硫酰胺的方法包括以下步骤：在三价磷化合物和偶氮二甲酸衍生物存在下，使醇和氧羰基硫酰胺化合物反应。在一个实施方案中，硫酰胺由式 I 表示，醇由式 II 表示，氧羰基硫酰胺化合物由式 III 表示： R³NHSO₂NR¹R² (I) 其中 R¹ 和 R² 分别独立地选自氢、烷基、环烷基、烯基、炔基、芳烷基、芳基、杂环基和被杂环基取代的烷基组成的组，所述杂环基选自吡喃基、呋喃基、哌啶基、吡咯烷基、氮杂环丁酮环、头孢环、青霉环和碳青霉环组成的组；R³ 选自由烷基、烯基、炔基、芳基、杂环基、被杂环基取代的烷基和吡咯烷基甲基组成的组，所述杂环基选自由吡喃糖基、呋喃糖基、哌啶基、吡咯烷基、氮杂环丁酮环、头孢环、戊烯环和碳青霉烯环组成的组； R³OH (II) 其中 R³ 的定义同上； R⁴OOC-NHSO₂NR¹R² (III) 其中 R¹ 和 R² 的定义同上；R⁴ 是羧基保护基团。
• US5539102A
  申请人：——

  公开号：US5539102A

  公开（公告）日：1996-07-23
• Synthesis and evaluation of novel pyrrolidinyl sordaricin derivatives as antifungal agents
  作者：Masami Arai、Tamako Harasaki、Takashi Fukuoka、Satoru Kaneko、Toshiyuki Konosu

  DOI：10.1016/s0960-894x(02)00534-6

  日期：2002.10

  N-Benzyl pyrrolidinyl sordaricin derivatives have been synthesized from cis-4-hydroxy-D-proline in a stereocontrolled manner. These compounds maintained moderate antifungal activity against several pathogenic fungal strains. Their MIC values against Candida albicans were in the range of 0.25-2 mug/mL. (C) 2002 Elsevier Science Ltd. All rights reserved.