(S)-3-(benzyloxycarbonyl)-4-tert-butyl-[1,2,3]oxathiazolidine 2,2-dioxide | 1007121-77-8

• 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-tert-butyl-[1,2,3]oxathiazolidine 2,2-dioxide
• 英文别名: benzyl (4S)-4-tert-butyl-2,2-dioxooxathiazolidine-3-carboxylate
• CAS: 1007121-77-8
• 化学式: C₁₄H₁₉NO₅S
• 分子量: 313.375
• InChiKey: UZRFUZRIQNZYNW-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-tert-butyl-[1,2,3]oxathiazolidine 2,2-dioxide 、 N-烯丙基对甲苯磺酰胺 在 氢氧化钾 、 盐酸 作用下， 以 乙腈 、 乙酸乙酯 为溶剂， 以89%的产率得到benzyl (S)-1-(N-allyl-4-methylbenzenesulfonamido)-3,3-dimethylbutan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction

  摘要：

  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.

  DOI：

  10.1021/ol702891p
• 作为产物：
  描述：

  N-carbobenzoxy-L-tert-leucinol 在 ruthenium trichloride 氯化亚砜 、 吡啶 、 sodium periodate 、 水 作用下， 以 乙腈 为溶剂， 反应 1.02h， 以76%的产率得到(S)-3-(benzyloxycarbonyl)-4-tert-butyl-[1,2,3]oxathiazolidine 2,2-dioxide
  参考文献：
  名称：

  Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction

  摘要：

  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.

  DOI：

  10.1021/ol702891p

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。
• 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.