(S)-2-(3-t-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl)-1,3-thiazole-4-thiocarboxamide | 478937-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-2-(3-t-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl)-1,3-thiazole-4-thiocarboxamide
• 英文别名: tert-butyl (4S)-4-(4-carbamothioyl-1,3-thiazol-2-yl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 478937-39-2
• 化学式: C₁₄H₂₁N₃O₃S₂
• 分子量: 343.471
• InChiKey: HITNAPHPWNAEJP-VIFPVBQESA-N

物化性质

• 沸点：
  475.8±55.0 °C(predicted)
• 密度：
  1.272±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-(3-t-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl)-1,3-thiazole-4-thiocarboxamide 在 lithium hydroxide monohydrate 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 11.33h， 生成 2-[2-[2-[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]-1,3-thiazol-4-yl]-1,3-thiazol-4-yl]-5-phenyl-1,3-oxazole-4-carboxylic acid
  参考文献：
  名称：

  Total Synthesis and Biological Activity of Natural Product Urukthapelstatin A

  摘要：

  Herein we report the first total synthesis of the natural product Urkuthaplestatin A (Ustat A) utilizing a convergent synthetic strategy. The characterization and biological activity match those of the previously published natural product. Interestingly, several intermediates, including the linear and serine cyclized precursors, show a 100-fold decrease in cytotoxicity, with IC50's in the low micromolar range. These data indicate that the rigidity and the consecutive aromatic heterocyclic system are responsible for the biological activity.

  DOI：

  10.1021/ol401412v
• 作为产物：
  描述：

  (S)-(-)-3-BOC-4-甲氧羰基-2,2-二甲基-1,3-恶唑烷 在 劳森试剂 、 ammonium hydroxide 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 苯 为溶剂， 反应 48.0h， 生成 (S)-2-(3-t-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl)-1,3-thiazole-4-thiocarboxamide
  参考文献：
  名称：

  Total Synthesis and Biological Activity of Natural Product Urukthapelstatin A

  摘要：

  Herein we report the first total synthesis of the natural product Urkuthaplestatin A (Ustat A) utilizing a convergent synthetic strategy. The characterization and biological activity match those of the previously published natural product. Interestingly, several intermediates, including the linear and serine cyclized precursors, show a 100-fold decrease in cytotoxicity, with IC50's in the low micromolar range. These data indicate that the rigidity and the consecutive aromatic heterocyclic system are responsible for the biological activity.

  DOI：

  10.1021/ol401412v

文献信息

• Novel Synthesis of the Main Central 2,3,6-Trisubstituted Pyridine Skeleton [Fragment A-B-C] of a Macrobicyclic Antibiotic, Cyclothiazomycin
  作者：Chung-gi Shin、Akihiro Okabe、Akinori Ito、Akio Ito、Yasuchika Yonezawa

  DOI：10.1246/bcsj.75.1583

  日期：2002.7

  the protected Ser thioamide derivative with 3-bromopyruvate, and then thiazolination of the C-terminal Ser residue of the sequence. Secondly, an efficient synthesis of the central 2-(2-2-[(1R)-1-aminoethyl]pyridin-6-yl}thiazol-4-yl)-4,5-dihydrothiazole-4-carboxylate [Fragment B derivative] was also achieved by thiazolation of the formyl group of the 2-(1-aminoethyl)-6-formylpyridine derivative, and

  首先完成了大双环抗生素环噻霉素的主要中央 2,3,6-三取代吡啶骨架 [受保护的片段 ABC] 的有用合成。首先，连接到主要吡啶骨架的 6-取代基上的 2-[2-(2-取代的噻唑-4-基)]-4,5-二氢噻唑-4-羧酸酯 [片段 A 衍生物] 是由以下合成的：用 3-溴丙酮酸对受保护的 Ser 硫代酰胺衍生物进行两次连续的噻唑化，然后对序列的 C 端 Ser 残基进行噻唑化。其次，有效合成中心 2-(2-2-[(1R)-1-aminoethyl]pyridin-6-yl}thiazol-4-yl)-4,5-dihydrothiazole-4-carboxylate [片段 B [衍生物]也通过2-(1-氨基乙基)-6-甲酰基吡啶衍生物的甲酰基的噻唑化，然后噻唑化来实现。第三，
• Total Synthesis and Biological Activity of Natural Product Urukthapelstatin A
  作者：Chun-Chieh Lin、Worawan Tantisantisom、Shelli R. McAlpine

  DOI：10.1021/ol401412v

  日期：2013.7.19

  Herein we report the first total synthesis of the natural product Urkuthaplestatin A (Ustat A) utilizing a convergent synthetic strategy. The characterization and biological activity match those of the previously published natural product. Interestingly, several intermediates, including the linear and serine cyclized precursors, show a 100-fold decrease in cytotoxicity, with IC50's in the low micromolar range. These data indicate that the rigidity and the consecutive aromatic heterocyclic system are responsible for the biological activity.