[(4R,5S)-3-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-acetyl]-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester | 877814-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(4R,5S)-3-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-acetyl]-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester
• 英文别名: prop-2-enyl 2-[(4R,5S)-3-[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]-4-[(4-methoxyphenyl)methylsulfanylmethyl]-2-oxo-1,3-oxazolidin-5-yl]acetate
• CAS: 877814-37-4
• 化学式: C₃₄H₃₄N₂O₈S
• 分子量: 630.719
• InChiKey: FVNZFNFKOFIOGR-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(4R,5S)-3-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-acetyl]-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester 在 四(三苯基膦)钯 N-甲基吗啉 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以100%的产率得到[(4R,5S)-3-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-acetyl]-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid
  参考文献：
  名称：

  Cysteine-Derived S-Protected Oxazolidinones:  Potential Chemical Devices for the Preparation of Peptide Thioesters

  摘要：

  [GRAPHICS]An N-S acyl-transfer-mediated preparation of peptide thioesters using the S-protected oxazolidinone derived from cysteine has been developed and applied to the synthesis of a 32-mer biologically active peptide by native chemical ligation protocols.

  DOI：

  10.1021/ol052755m
• 作为产物：
  描述：

  烯丙基2-溴乙酸乙酯 在 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.67h， 生成 [(4R,5S)-3-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-acetyl]-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester
  参考文献：
  名称：

  Cysteine-Derived S-Protected Oxazolidinones:  Potential Chemical Devices for the Preparation of Peptide Thioesters

  摘要：

  [GRAPHICS]An N-S acyl-transfer-mediated preparation of peptide thioesters using the S-protected oxazolidinone derived from cysteine has been developed and applied to the synthesis of a 32-mer biologically active peptide by native chemical ligation protocols.

  DOI：

  10.1021/ol052755m

文献信息

• Cysteine-Derived <i>S</i>-Protected Oxazolidinones:  Potential Chemical Devices for the Preparation of Peptide Thioesters
  作者：Yusuke Ohta、Saori Itoh、Akira Shigenaga、Saori Shintaku、Nobutaka Fujii、Akira Otaka

  DOI：10.1021/ol052755m

  日期：2006.2.1

  [GRAPHICS]An N-S acyl-transfer-mediated preparation of peptide thioesters using the S-protected oxazolidinone derived from cysteine has been developed and applied to the synthesis of a 32-mer biologically active peptide by native chemical ligation protocols.