ethyl (4S)-3-benzyl-2,2-dioxooxathiazolidine-4-carboxylate | 211292-18-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (4S)-3-benzyl-2,2-dioxooxathiazolidine-4-carboxylate
• CAS: 211292-18-1
• 化学式: C₁₂H₁₅NO₅S
• 分子量: 285.321
• InChiKey: WXODYTSNOGLCGR-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (4S)-3-benzyl-2,2-dioxooxathiazolidine-4-carboxylate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 56.0h， 生成 tetraethyl (2S,6S,11S,15S)-1,7,10,16-tetrabenzyl-4,13-bis[(4-methoxyphenyl)methyl]-1,4,7,10,13,16-hexazacyclooctadecane-2,6,11,15-tetracarboxylate
  参考文献：
  名称：

  A short synthesis of chiral peraza-macrocycles through opening of cyclic sulfamidates

  摘要：

  Efficient and general synthetic methods for novel chiral peraza-macrocycles have been developed. Sequential reactions of the known cyclic sulfamidate 4 derived from N-benzyl-L-serine methyl ester with p-methoxybenzylamine provided a symmetric triamine 3, which served as a building block for the construction of various chiral peraza-macrocycles. Reaction of the triamine. with a proper connecting unit provided [18]-N-6 or [10]-N-3 chiral peraza-macrocycles. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01545-2
• 作为产物：
  描述：

  N-benzylserine ethyl ester 生成 ethyl (4S)-3-benzyl-2,2-dioxooxathiazolidine-4-carboxylate
  参考文献：
  名称：

  使用路易斯酸和硫醇高效水解β-氨基氨基磺酸以合成2,3-二氨基丙酸酯衍生物

  摘要：

  已经开发了由与各种伯或仲胺的环状氨基磺酸酯的开环产生的β-氨基氨基磺酸的新的水解条件。这种新的水解方法使我们能够使用最多两个当量的胺亲核试剂，以良好或极好的收率得到2,3-二氨基丙酸酯衍生物。

  DOI：

  10.1016/s0040-4039(98)01079-x

文献信息

• A Short Synthesis of Conformationally Constrained Unnatural Bicyclic Amino Acids Containing a Nitrogen Atom at the Ring Juncture: (9a<i>R</i>)- and (9a<i>S</i>)-Octahydropyrido[1,2-<i>a</i>]pyrazine-(3<i>S</i>)-carboxylic Acids (Opc)
  作者：B. Kim、Soon So、Chang-Eun Yeom、Seong Cho、Soo Choi、Young Chung

  DOI：10.1055/s-2008-1042762

  日期：——

  A short and efficient route to conformationally constrained amino acid analogues, (9a R)- and (9a S)-octahydropyrido[1,2- A]pyrazine-(3 S)-carboxylate (Opc) has been developed. The new bicyclic amino acid derivatives can be stored and utilized as a modular unit for the construction of unnatural oligopeptides using conventional peptide coupling methods.

  已经开发了一种获得构象受限的氨基酸类似物（9a R）-和（9a S）-八氢吡啶并[1,2-A]吡嗪-（3 S）-羧酸盐（Opc）的短而有效的途径。新的双环氨基酸衍生物可以储存并用作模块化单元，用于使用常规肽偶联方法构建非天然寡肽。
• A short synthesis of chiral peraza-macrocycles through opening of cyclic sulfamidates
  作者：B.Moon Kim、Soon Mog So

  DOI：10.1016/s0040-4039(99)01545-2

  日期：1999.10

  Efficient and general synthetic methods for novel chiral peraza-macrocycles have been developed. Sequential reactions of the known cyclic sulfamidate 4 derived from N-benzyl-L-serine methyl ester with p-methoxybenzylamine provided a symmetric triamine 3, which served as a building block for the construction of various chiral peraza-macrocycles. Reaction of the triamine. with a proper connecting unit provided [18]-N-6 or [10]-N-3 chiral peraza-macrocycles. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Efficient hydrolysis of β-aminosulfamic acids using a Lewis acid and a thiol for the synthesis of 2,3-diaminopropanoate derivatives
  作者：B.Moon Kim、Soon Mog So

  DOI：10.1016/s0040-4039(98)01079-x

  日期：1998.7

  New hydrolysis conditions for β-aminosulfamic acids produced from the opening of a cyclic sulfamidate with a variety of primary or secondary amines have been developed. This new hydrolysis method allowed us to use at most two equivalents of amine nucleophiles furnishing 2,3-diaminopropanoate derivatives in good to excellent yields.

  已经开发了由与各种伯或仲胺的环状氨基磺酸酯的开环产生的β-氨基氨基磺酸的新的水解条件。这种新的水解方法使我们能够使用最多两个当量的胺亲核试剂，以良好或极好的收率得到2,3-二氨基丙酸酯衍生物。