(3aS,4S,6aR)-4-hept-6-ynyl-2-oxo-tetrahydro-thieno[3,4-d]imidazole-1,3-dicarboxylic acid di-tert-butyl ester | 887915-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并咪唑类化合物
• 英文名称: (3aS,4S,6aR)-4-hept-6-ynyl-2-oxo-tetrahydro-thieno[3,4-d]imidazole-1,3-dicarboxylic acid di-tert-butyl ester
• 英文别名: ditert-butyl (3aS,4S,6aR)-4-hept-6-ynyl-2-oxo-3a,4,6,6a-tetrahydrothieno[3,4-d]imidazole-1,3-dicarboxylate
• CAS: 887915-54-0
• 化学式: C₂₂H₃₄N₂O₅S
• 分子量: 438.588
• InChiKey: XHMNKNUBVOYGTL-ULQDDVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6aR)-4-hept-6-ynyl-2-oxo-tetrahydro-thieno[3,4-d]imidazole-1,3-dicarboxylic acid di-tert-butyl ester 在 palladium diacetate lithium hydroxide 、 copper(l) iodide 、 二乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 9.5h， 生成 (2S)-2-amino-3-{4-[7-((3aS,4S,6aR)-2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-hept-1-ynyl]-phenyl}-propionic acid trifluoroacetate
  参考文献：
  名称：

  Synthesis of a Biotin-Derived Alkyne for Pd-Catalyzed Coupling Reactions

  摘要：

  An efficient synthesis of a terminal alkyne derived from cl biotin was developed to provide an alternative for carboxyl-based biotinylation. This approach was illustrated by the preparation of alkyne- and alkene-linked phenylalanine derivatives using palladium-catalyzed Sonogashira and Oh methodology. (Strept)avidin binding was observed using soluble and immobilized receptors. These results demonstrate the applicability of carbon-linked biotin derivatives for use in affinity-based purification and bioanalytical applications.

  DOI：

  10.1021/ol060458r
• 作为产物：
  描述：

  (3aS,4S,6aR)-4-hept-6-ynyl-tetrahydro-thieno[3,4-d]imidazol-2-one 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到(3aS,4S,6aR)-4-hept-6-ynyl-2-oxo-tetrahydro-thieno[3,4-d]imidazole-1,3-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  Synthesis of a Biotin-Derived Alkyne for Pd-Catalyzed Coupling Reactions

  摘要：

  An efficient synthesis of a terminal alkyne derived from cl biotin was developed to provide an alternative for carboxyl-based biotinylation. This approach was illustrated by the preparation of alkyne- and alkene-linked phenylalanine derivatives using palladium-catalyzed Sonogashira and Oh methodology. (Strept)avidin binding was observed using soluble and immobilized receptors. These results demonstrate the applicability of carbon-linked biotin derivatives for use in affinity-based purification and bioanalytical applications.

  DOI：

  10.1021/ol060458r

文献信息

• Synthesis of a Biotin-Derived Alkyne for Pd-Catalyzed Coupling Reactions
  作者：Cesear Corona、Bj K. Bryant、Jeffrey B. Arterburn

  DOI：10.1021/ol060458r

  日期：2006.4.1

  An efficient synthesis of a terminal alkyne derived from cl biotin was developed to provide an alternative for carboxyl-based biotinylation. This approach was illustrated by the preparation of alkyne- and alkene-linked phenylalanine derivatives using palladium-catalyzed Sonogashira and Oh methodology. (Strept)avidin binding was observed using soluble and immobilized receptors. These results demonstrate the applicability of carbon-linked biotin derivatives for use in affinity-based purification and bioanalytical applications.