(S)-3-(benzyloxycarbonyl)-4-benzyl-[1,2,3]oxathiazolidine 2,2-dioxide | 1007121-75-6

• 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: (S)-3-(benzyloxycarbonyl)-4-benzyl-[1,2,3]oxathiazolidine 2,2-dioxide
• 英文别名: benzyl (4S)-4-benzyl-2,2-dioxo-1,2,3-oxathiazolidine-3-carboxylate；aminosultone；(S)-3-Cbz-4-benzyl-1,2,3-oxathiazolidine 2,2-dioxide；benzyl (4S)-4-benzyl-2,2-dioxooxathiazolidine-3-carboxylate
• CAS: 1007121-75-6
• 化学式: C₁₇H₁₇NO₅S
• 分子量: 347.392
• InChiKey: WKUGEFRCNJWDJK-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(benzyloxycarbonyl)-4-benzyl-[1,2,3]oxathiazolidine 2,2-dioxide 在 silver hexafluoroantimonate 、 三苯基膦氯金 、 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.17h， 生成 benzyl (2S)-6-methyl-4-[(2-nitrobenzene)sulfonyl]-2-benzyl-1,2,3,4-tetrahydropyrazine-1-carboxylate
  参考文献：
  名称：

  Modular, Gold-Catalyzed Approach to the Synthesis of Lead-like Piperazine Scaffolds

  摘要：

  Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.

  DOI：

  10.1021/ol402988s
• 作为产物：
  描述：

  Z-L-苯丙氨醇 在 咪唑 、 sodium periodate 、 氯化亚砜 、 ruthenium(III) chloride trihydrate 、 水 、 三甲胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (S)-3-(benzyloxycarbonyl)-4-benzyl-[1,2,3]oxathiazolidine 2,2-dioxide
  参考文献：
  名称：

  环磺酰胺酸盐和硫酸盐与氟二(苯磺酰基)甲烷的 α-氟碳负离子和 2-氟乙酰乙酸乙酯的单氟甲基化

  摘要：

  已经开发出环状磺酰胺酯和硫酸酯与由氟代双（苯磺酰基）甲烷（FBSM）产生的α-氟碳负离子进行开环以及随后的还原脱磺酰化。这种氟甲基化方法可以高产率地获得 γ- 和 δ- 氟胺以及 γ- 和 δ- 氟醇。还描述了环状磺酰胺与 2-氟乙酰乙酸乙酯的 α-氟碳负离子的单氟甲基化。

  DOI：

  10.1002/ejoc.202300651

文献信息

• Copper-Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β-and γ-Amino­alkyl)boronic Esters
  作者：Nina Ursinyova、Robin B. Bedford、Timothy Gallagher

  DOI：10.1002/ejoc.201501492

  日期：2016.2

  Abstract Cyclic sulfamidates undergo borylation under copper‐catalyzed conditions using B2pin2 to give enantiomerically (and diasteromerically) defined (aminoalkyl)boronic esters. External iodide is essential, but the intermediacy of simple alkyl iodides has been excluded; N‐sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement

  摘要 环状磺酰胺在铜催化条件下使用 B2pin2 进行硼酸化，得到对映异构（和非对映异构）定义的（氨基烷基）硼酸酯。外部碘化物是必不可少的，但简单的烷基碘化物已被排除在外；N-硫酸化中间体是硼酸化序列中的关键。基于立体化学研究和捕获实验，在这些铜催化条件下碳中心自由基的参与似乎是可能的。
• Spiro-fused Pyrrolidine, Piperidine, and Oxindole Scaffolds from Lactams
  作者：Christoph Hirschhäuser、Jeremy S. Parker、Matthew W. D. Perry、Mairi F. Haddow、Timothy Gallagher

  DOI：10.1021/ol302176z

  日期：2012.9.21

  Expedient routes to three classes of novel spiro-fused pyrrolidine, piperidine, and indoline heterocycle scaffolds are described. These three-dimensional frameworks, which conform to the “rule of three”, are suitably protected to allow for site-selective manipulation and functionalization. Different modes of substrate control were explored, which allow for good to excellent levels of diastereoselectivity

  描述了三类新型螺-稠合的吡咯烷，哌啶和二氢吲哚杂环骨架的权宜之路。符合“三个规则”的这些三维框架得到了适当的保护，可以进行位点选择操作和功能化。探索了不同的底物控制模式，可以实现良好至极好的非对映选择性，并且无需使用其他手性试剂或催化剂。所开发的概念适用于（±）-coerulescine和（±）-horsfiline的简短正式合成。
• Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction
  作者：Brian M. Cochran、Forrest E. Michael

  DOI：10.1021/ol702891p

  日期：2008.1.1

  A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic displacement of cyclic sulfamidates derived from amino acids. A variety of alkyl and aryl substituents at the 2-position were tolerated. The stereochemistry of the piperazines was determined to be trans by X-ray crystallography, which also showed the preferred conformation of the 2,6-disubstituted piperazine to be a twist-boat due to A(1,3) strain.
• CN116606232
  申请人：——

  公开号：——

  公开（公告）日：——
• Modular, Gold-Catalyzed Approach to the Synthesis of Lead-like Piperazine Scaffolds
  作者：Thomas James、Iain Simpson、J. Andrew Grant、Visuvanathar Sridharan、Adam Nelson

  DOI：10.1021/ol402988s

  日期：2013.12.6

  Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.