benzyl [(4R)-3-oxo-1,2-oxazolidin-4-yl]carbamate | 28832-02-2

• 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: benzyl [(4R)-3-oxo-1,2-oxazolidin-4-yl]carbamate
• 英文别名: N-benzyloxycarbonyl-D-4-amino-3-isoxazolidinone；N-((benzyloxy)carbonyl)-D-cycloserine；(R)-benzyloxycarbonyl-cycloserine；Cbz-D-cycloserine；((R)-3-oxo-isoxazolidin-4-yl)-carbamic acid benzyl ester；N-Benzyloxycarbonyl-D-cycloserin；(4R)-4-benzyloxycarbonylamino-3-isoxazolidinone；benzyl N-[(4R)-3-oxo-1,2-oxazolidin-4-yl]carbamate
• CAS: 28832-02-2
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: WTWQPRDBXUERAW-SECBINFHSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl [(4R)-3-oxo-1,2-oxazolidin-4-yl]carbamate 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.33h， 生成
  参考文献：
  名称：

  O-Sulfated .beta.-lactam hydroxamic acids (monosulfactams). Novel monocyclic .beta.-lactam antibiotics of synthetic origin

  摘要：

  DOI：

  10.1021/ja00386a035
• 作为产物：
  描述：

  氯甲酸苄酯 在 N-甲基吗啉 、 氯甲酸乙酯 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 benzyl [(4R)-3-oxo-1,2-oxazolidin-4-yl]carbamate
  参考文献：
  名称：

  有效且简便地合成基本不含潜在杂质的D-环丝氨酸

  摘要：

  已经从D-丝氨酸开发了一种有效且容易的D-环丝氨酸合成方法，采用保护脱保护策略，总收率达61％。研究了影响D-环丝氨酸杂质含量和产率的不同参数。温和的反应条件为产品提供了卓越的纯度（> 99％）和高稳定性。

  DOI：

  10.1007/s10593-018-2197-y

文献信息

• Synthesis of lactivicin and its derivatives
  作者：Hideaki Natsugari、Yasuhiko Kawano、Akira Morimoto、Kouichi Yoshioka、Michihiko Ochiai

  DOI：10.1039/c39870000062

  日期：——

  Lactivicin, a new type of antibiotic having β-lactam-like activity, and its derivatives were synthesized starting from 4-benzyloxycarbonylamino-3-isoxazolidinones and 2-oxoglutaric acid.

  以4-苄氧基羰基氨基-3-异恶唑烷酮和2-氧戊二酸为原料，合成了具有β-内酰胺样活性的新型抗生素Lactivicin及其衍生物。
• Antibiotic
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04851422A1

  公开（公告）日：1989-07-25

  The compound represented by the formula: ##STR1## where R.sup.1 stands for amino or an organic residue bonded through nitrogen; R.sup.2 stands for carboxyl or a group derivable therefrom; R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently stand for hydrogen or an organic residue, including the case where R.sup.5 or R.sup.6 forms a chemical bond or a ring with R.sup.7 or R.sup.8 ; X stands for hydrogen, methoxy or formylamino; or a salt thereof, produceable by the present method, exhibits excellent antimicrobial activity, and is utilized as antimicrobial agents.

  化学式为：##STR1## 其中R1代表氨基或通过氮键合的有机残基；R2代表羧基或可由其衍生的基团；R3、R4、R5、R6、R7和R8独立地代表氢或有机残基，包括R5或R6与R7或R8形成化学键或环的情况；X代表氢、甲氧基或甲酰氨基；或其盐，由本方法生产的化合物表现出优异的抗微生物活性，并用作抗微生物剂。
• Antibiotic derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0219923A1

  公开（公告）日：1987-04-29

  The compound represented by the formula: where R' stands for amino or an organic residue bonded through nitrogen; R2 stands for carooxyl ora group derivable therefrom; R3, R4, R5, R6, R7 and R8 independently stand for hydrogen or an organic residue, including the case where R5 or R6 forms a chemical bond or a ring with R7 or R8: X stands for hvdrogen, methoxy or formylamino; or a salt thereof, pro- duceaole by the present method. exnibits excellent antimicrobial activity, and is utilized as antimicrobial agents.

  式所代表的化合物： 其中，R'代表氨基或通过氮键结合的有机残基；R2代表甲氧羰基或可由其衍生的基团；R3、R4、R5、R6、R7 和 R8 分别代表氢或有机残基，包括 R5 或 R6 与 R7 或 R8 形成化学键或环状的情况：X 代表氢、甲氧基或甲酰氨基；或其盐，通过本方法制得。它们具有优异的抗菌活性，可用作抗菌剂。
• Pharmacophore Assessment Through 3-D QSAR: Evaluation of the Predictive Ability on New Derivatives by the Application on a Series of Antitubercular Agents
  作者：Laura Friggeri、Flavio Ballante、Rino Ragno、Ira Musmuca、Daniela De Vita、Fabrizio Manetti、Mariangela Biava、Luigi Scipione、Roberto Di Santo、Roberta Costi、Marta Feroci、Silvano Tortorella

  DOI：10.1021/ci400132q

  日期：2013.6.24

  Pharmacophoric mapping is a useful procedure to frame, especially, when crystallographic receptor structures are unavailable as in ligand-based studies, the hypothetical site of interaction. In this study, 71 pyrrole derivatives active against M. tuberculosis, were used to derive through a recent new 3-D QSAR protocol; 3-D QSAutogrid/R, several predictive 3-D QSAR models on compounds aligned by a previously reported pharmacophoric application. A final multiprobe (MP) 3-D QSAR model was then obtained configuring itself as a tool to derive pharmacophoric quantitative models. To stress the applicability of the described models, an external test set of unrelated and newly synthesized series of R-4-amino-3-isoxazolidinone derivatives found to be active at micromolar level against M. tuberculosis was used, and the predicted bioactivities were in good agreement with the experimental values. The 3-D QSAutogrid/R procedure proved to be able to correlate by a single multi-informative scenario the,different activity molecular profiles thus confirming its usefulness in the rational drug design approach.
• Cycloserine derivatives
  作者：Charles H. Stammer、C. Chandrasekharan Kartha、Nishith C. Chaturvedi、James D. McKinney

  DOI：10.1021/jm00299a063

  日期：1970.9