Boc-L-Ser(tBu)-L,D-PheSer-OMe | 930285-06-6

• 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: Boc-L-Ser(tBu)-L,D-PheSer-OMe
• 英文别名: Boc-Ser(tBu)-DL-Phe(b-OH)-OMe；methyl 3-hydroxy-2-[[(2S)-3-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-phenylpropanoate
• CAS: 930285-06-6
• 化学式: C₂₂H₃₄N₂O₇
• 分子量: 438.521
• InChiKey: AMLIACNOVBXPOV-GTPINHCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-L-Ser(tBu)-L,D-PheSer-OMe 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  Synthesis of IB-01211, a Cyclic Peptide Containing 2,4-Concatenated Thia- and Oxazoles, via Hantzsch Macrocyclization

  摘要：

  An efficient and versatile convergent synthesis of IB-01211 based on a combination of peptide and heterocyclic chemistry is described. The key step in the synthesis is macrocyclization through intramolecular Hantzsch formation of the thiazole ring. Dehydration of a free primary alcohol to furnish the exocyclic methylidene present in the natural product was applied during the macrocyclization.

  DOI：

  10.1021/ol063023c
• 作为产物：
  描述：

  N-叔丁氧羰基-O-叔丁基-L-丝氨酸 、 D,L-phenylserine methyl ester hydrochloride 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以100%的产率得到Boc-L-Ser(tBu)-L,D-PheSer-OMe
  参考文献：
  名称：

  Synthesis of IB-01211, a Cyclic Peptide Containing 2,4-Concatenated Thia- and Oxazoles, via Hantzsch Macrocyclization

  摘要：

  An efficient and versatile convergent synthesis of IB-01211 based on a combination of peptide and heterocyclic chemistry is described. The key step in the synthesis is macrocyclization through intramolecular Hantzsch formation of the thiazole ring. Dehydration of a free primary alcohol to furnish the exocyclic methylidene present in the natural product was applied during the macrocyclization.

  DOI：

  10.1021/ol063023c

文献信息

• Synthesis of IB-01211, a Cyclic Peptide Containing 2,4-Concatenated Thia- and Oxazoles, via Hantzsch Macrocyclization
  作者：Delia Hernández、Gemma Vilar、Estela Riego、Librada M. Cañedo、Carmen Cuevas、Fernando Albericio、Mercedes Álvarez

  DOI：10.1021/ol063023c

  日期：2007.3.1

  An efficient and versatile convergent synthesis of IB-01211 based on a combination of peptide and heterocyclic chemistry is described. The key step in the synthesis is macrocyclization through intramolecular Hantzsch formation of the thiazole ring. Dehydration of a free primary alcohol to furnish the exocyclic methylidene present in the natural product was applied during the macrocyclization.