Tert-butyl 5-benzyl-1,1,4-trioxo-1,2,5-thiadiazolidine-2-carboxylate | 1131454-43-7

• 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: Tert-butyl 5-benzyl-1,1,4-trioxo-1,2,5-thiadiazolidine-2-carboxylate
• CAS: 1131454-43-7
• 化学式: C₁₄H₁₈N₂O₅S
• 分子量: 326.373
• InChiKey: VKTNZADTDVMMHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl 5-benzyl-1,1,4-trioxo-1,2,5-thiadiazolidine-2-carboxylate 、 2-硫代水杨醛 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到
  参考文献：
  名称：

  Activated sulfahydantoin as Boc-glycine enolate equivalent: highly diastereoselective α-hydroxyalkylation and application to the synthesis of aldopentonate analogues

  摘要：

  N-Boc-activated sulfahydantoin can be seen as glycine enolate equivalent. It appeared as a convenient starting material for the stereocontrolled preparation of threonine homologues through an alkaline syn aldolization involving a Boc migration. The methodology allowed the one-pot preparation of constrained analogues of polyoxamic acid. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.070
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 苄胺 、 N-sulfonyloxazolidinone 在 sodium ethanolate 、 4-二甲氨基吡啶 作用下， 以 乙腈 、 乙醇 为溶剂， 以50%的产率得到Tert-butyl 5-benzyl-1,1,4-trioxo-1,2,5-thiadiazolidine-2-carboxylate
  参考文献：
  名称：

  Activated sulfahydantoin as Boc-glycine enolate equivalent: highly diastereoselective α-hydroxyalkylation and application to the synthesis of aldopentonate analogues

  摘要：

  N-Boc-activated sulfahydantoin can be seen as glycine enolate equivalent. It appeared as a convenient starting material for the stereocontrolled preparation of threonine homologues through an alkaline syn aldolization involving a Boc migration. The methodology allowed the one-pot preparation of constrained analogues of polyoxamic acid. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.070

文献信息

• Activated sulfahydantoin as Boc-glycine enolate equivalent: highly diastereoselective α-hydroxyalkylation and application to the synthesis of aldopentonate analogues
  作者：Djamel Bouchouk、Evelina Colacino、Loïc Toupet、Noureddine Aouf、Jean Martinez、Georges Dewynter

  DOI：10.1016/j.tetlet.2008.12.070

  日期：2009.3

  N-Boc-activated sulfahydantoin can be seen as glycine enolate equivalent. It appeared as a convenient starting material for the stereocontrolled preparation of threonine homologues through an alkaline syn aldolization involving a Boc migration. The methodology allowed the one-pot preparation of constrained analogues of polyoxamic acid. (C) 2008 Elsevier Ltd. All rights reserved.