(3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone | 99397-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone
• 英文别名: (3S,4S)-3-<(benzyloxycarbonyl)amino>-4-(85hydroxymethyl)-2-azetidinone；(3S,4S) 3-<(benzyloxycarbonyl)amino>-4-(hydroxymethyl)-2-azetidinone；(3S,4S) 3-<(benzyloxycarbonyl)amino>-4-hydroxymethyl-2-azetidinone；(2S,3S)-methyl 3-(benzyloxycarbonylamino)-4-oxoazetidine-2-carboxylate；(3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethylazetidin-2-one；benzyl ((2S,3S)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate；benzyl N-[(2S,3S)-2-(hydroxymethyl)-4-oxoazetidin-3-yl]carbamate
• CAS: 99397-29-2
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: SAKPMXDWJXMKQH-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone 在 sodium N-methyldithiocarbamate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 3,4-cis-3-benzyloxycarbonylamino-4-carbamoyloxymethyl-2-azetidione
  参考文献：
  名称：

  通过手性3-羟基酯的亲电胺化反应合成顺式单bactams的对映体和非对映选择性

  摘要：

  据报道，从β-羟基酯开始新的有效进入顺式单bactams的方法。该制备基于β-羟基酯二价阴离子的立体选择性“亲电胺化”和β-内酰胺核的米勒仿生合成。通过这种途径，制备了用于制备具有药理学意义的顺式氨曲南2和卡鲁米南3的关键中间体。

  DOI：

  10.1016/s0040-4020(01)89308-x
• 作为产物：
  描述：

  (2S,3S)-ethyl 3-(((benzyloxy)carbonyl)amino)-4-oxoazetidine-2-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到(3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone
  参考文献：
  名称：

  SAR and Structural Analysis of Siderophore-Conjugated Monocarbam Inhibitors of Pseudomonas aeruginosa PBP3

  摘要：

  A main challenge in the development of new agents for the treatment of Pseudomonas aeruginosa infections is the identification of chemotypes that efficiently penetrate the cell envelope and are not susceptible to established resistance mechanisms. Siderophore-conjugated monocarbams are attractive because of their ability to hijack the bacteria's iron uptake machinery for transport into the periplasm and their inherent stability to metallo-beta-lactamases. Through development of the SAR we identified a number of modifications to the scaffold that afforded active anti-P. aeruginosa agents with good physicochemical properties. Through crystallographic efforts we gained a better understanding into how these compounds bind to the target penicillin binding protein PBP3 and factors to consider for future design.

  DOI：

  10.1021/acsmedchemlett.5b00026

文献信息

• MONOBACTAM ORGANIC COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS
  申请人：AULAKH Virender Singh

  公开号：US20150266867A1

  公开（公告）日：2015-09-24

  This invention pertains generally to antibacterial compounds of Formula I, as further described herein, and pharmaceutically acceptable salts and formulations thereof. In certain aspects, the invention pertains to methods of using such compounds to treat infections such as those caused by Gram-negative bacteria.

  这项发明通常涉及公式I的抗菌化合物，如本文进一步描述，并其药用盐和制剂。在某些方面，该发明涉及使用这些化合物治疗由革兰氏阴性细菌引起的感染的方法。
• [EN] MONOBACTAMS<br/>[FR] MONOBACTAMES
  申请人：PFIZER

  公开号：WO2012073138A1

  公开（公告）日：2012-06-07

  The present invention is directed to a new class of monobactam derivatives and their use for treating bacterial infections.

  本发明涉及一类新的单环内酰胺衍生物及其用于治疗细菌感染的用途。
• Tricyclic cepham compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04891427A1

  公开（公告）日：1990-01-02

  The compounds having a 4,11-dioxo-3-oxa-8(or 7)-thia-1-azatricyclo[7,2,0,0.sup.2,6 ]undecane-2-carboxylic acid skeleton as the base structure, their esters and their salts are useful antibacterial agents.

  这些具有4,11-二氧-3-氧-8（或7）-硫-1-氮杂七环[7,2,0,0.sup.2,6]十一烷-2-羧酸骨架作为基本结构的化合物，它们的酯和盐是有用的抗菌剂。
• The asymmetric synthesis of β-lactam antibiotics - I. application of chiral oxazolidones in the staudinger reaction.
  作者：David A. Evans、Eric B. Sjogren

  DOI：10.1016/s0040-4039(00)89250-3

  日期：1985.1

  The reactions of oxazolidone 1 with N-benzylimines proceed with exceptional levels of asymmetric induction to form the cycloadducts 2. Subsequent dissolving metal reduction affords the homochiral β-lactam derivatives 3 in good overall yield (eq 1).

  恶唑烷酮1与N-苄基亚胺的反应以异常水平的不对称诱导进行，以形成环加合物2。随后的溶解金属还原以良好的总收率（eq 1）提供了同手性的β-内酰胺衍生物3。
• Optically active .beta.-lactams and method of their production
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04751299A1

  公开（公告）日：1988-06-14

  Optically active .beta.-lactams of the general formula ##STR1## wherein R.sup.1 is an amino or protected amino group, R.sup.2 is an organic residue bonding through a carbon atom thereof and R.sup.3 is the residue remaining after removal of the .alpha.-amino group from an optically active .alpha.-amino acid or a derivative thereof as well as a method of producing the same.

  具有一般式##STR1##的光学活性β-内酰胺，其中R.sup.1是氨基或保护氨基基团，R.sup.2是通过碳原子键合的有机残基，R.sup.3是在从光学活性α-氨基酸或其衍生物中去除α-氨基团后剩余的残留物，以及生产这种化合物的方法。