methyl 2-[(1S,2R)-1-[[2-[(1R)-2-tert-butylsulfanyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-5-methyl-1,3-oxazole-4-carbonyl]amino]-2-hydroxypropyl]-1,3-oxazole-4-carboxylate | 912656-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-[(1S,2R)-1-[[2-[(1R)-2-tert-butylsulfanyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-5-methyl-1,3-oxazole-4-carbonyl]amino]-2-hydroxypropyl]-1,3-oxazole-4-carboxylate
• CAS: 912656-45-2
• 化学式: C₂₄H₃₆N₄O₈S
• 分子量: 540.638
• InChiKey: RMJMMWDUEXASAH-KCXAZCMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  191
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2-[(1S,2R)-1-[[2-[(1R)-2-tert-butylsulfanyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-5-methyl-1,3-oxazole-4-carbonyl]amino]-2-hydroxypropyl]-1,3-oxazole-4-carboxylate 在 4-二甲氨基吡啶 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 伯吉斯试剂 、 4 A molecular sieve 、 叠氮磷酸二苯酯 、 1-羟基苯并三唑 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 95.0h， 生成 (12Z,22Z,32Z,72Z,82Z,92Z,12R)-6-(bromomethyl)-12-((tert-butylthio)methyl)-6-methoxy-15,25-dimethyl-5,11-diaza-1(2,4),2,3,7,8,9(4,2)-hexaoxazolacyclododecaphane-4,10-dione
  参考文献：
  名称：

  Total Synthesis of (R)-Telomestatin

  摘要：

  We have achieved a total synthesis of telomestatin, and its absolute configuration was determined to be (R). Coupling of cysteine-containing trisoxazole amine and serine-containing trisoxazole carboxylic acid, followed by macrocyclization, provided a 24-membered diamide. The seventh oxazole ring was formed by a Shin's procedure via dehydroamide. Cyclodehydration of a modified (R)-cysteine-(S-Bu-t) moiety using Kelly's method (PPh3(O)-Tf2O) with anisole furnished (R)-telomestatin, whose CD spectrum was in good agreement with that of the natural product.

  DOI：

  10.1021/ol061793i
• 作为产物：
  描述：

  N-叔丁氧羰基-S-叔丁基-L-半胱氨酸 在 lithium hydroxide 、 pyridine-SO3 complex 、 碘 、 1-羟基苯并三唑 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 methyl 2-[(1S,2R)-1-[[2-[(1R)-2-tert-butylsulfanyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-5-methyl-1,3-oxazole-4-carbonyl]amino]-2-hydroxypropyl]-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Total Synthesis of (R)-Telomestatin

  摘要：

  We have achieved a total synthesis of telomestatin, and its absolute configuration was determined to be (R). Coupling of cysteine-containing trisoxazole amine and serine-containing trisoxazole carboxylic acid, followed by macrocyclization, provided a 24-membered diamide. The seventh oxazole ring was formed by a Shin's procedure via dehydroamide. Cyclodehydration of a modified (R)-cysteine-(S-Bu-t) moiety using Kelly's method (PPh3(O)-Tf2O) with anisole furnished (R)-telomestatin, whose CD spectrum was in good agreement with that of the natural product.

  DOI：

  10.1021/ol061793i

文献信息

• Total Synthesis of (<i>R</i>)-Telomestatin
  作者：Takayuki Doi、Masahito Yoshida、Kazuo Shin-ya、Takashi Takahashi

  DOI：10.1021/ol061793i

  日期：2006.8.1

  We have achieved a total synthesis of telomestatin, and its absolute configuration was determined to be (R). Coupling of cysteine-containing trisoxazole amine and serine-containing trisoxazole carboxylic acid, followed by macrocyclization, provided a 24-membered diamide. The seventh oxazole ring was formed by a Shin's procedure via dehydroamide. Cyclodehydration of a modified (R)-cysteine-(S-Bu-t) moiety using Kelly's method (PPh3(O)-Tf2O) with anisole furnished (R)-telomestatin, whose CD spectrum was in good agreement with that of the natural product.