N-(benzyloxycarbonyl)ureido-N'-benzyloxycarbonyl-S-methylisothiourea

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(benzyloxycarbonyl)ureido-N'-benzyloxycarbonyl-S-methylisothiourea
• 英文别名: 5-(Methylthio)-3,7-dioxo-9-phenyl-8-oxa-2,4,6-triazanon-4-enoicAcidPhenylmethylEster；benzyl N-[methylsulfanyl-(phenylmethoxycarbonylcarbamoylamino)methylidene]carbamate
• 化学式: C₁₉H₁₉N₃O₅S
• 分子量: 401.443
• InChiKey: OTBMWJNXOGKKOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)ureido-N'-benzyloxycarbonyl-S-methylisothiourea 在 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (10S)-10-(((benzyloxy)carbonyl)amino)-14-((Z)-3-(((benzyloxy)carbonyl)imino)-5,7-dioxo-9-phenyl-8-oxa-2,4,6-triazanonyl)-5-imino-13-methyl-3,12-dioxo-1-phenyl-2-oxa-4,6,13-triazapentadecan-15-oic acid
  参考文献：
  名称：

  Total Synthesis of the Anti Methicillin-Resistant Staphylococcus aureus Peptide Antibiotics TAN-1057A-D

  摘要：

  TAN-1057A-D, dipeptides isolated from bacteria Flexibacter sp. PK-74 and PK-176, are new antibiotics with potent antibacterial activity against methicillin-resistant Staphylococcus aureus. We describe, in detail, the total synthesis of TAN-l057A-D by a convergent route featuring a new method to construct the cyclic amidinourea functional group.

  DOI：

  10.1021/ja972670j
• 作为产物：
  描述：

  benzyloxycarbonyl isocyanate 、 (Z)-benzyl amino(methylthio)methylenecarbamate 以 四氢呋喃 为溶剂， 反应 0.33h， 以100%的产率得到N-(benzyloxycarbonyl)ureido-N'-benzyloxycarbonyl-S-methylisothiourea
  参考文献：
  名称：

  Total Synthesis of the Anti Methicillin-Resistant Staphylococcus aureus Peptide Antibiotics TAN-1057A-D

  摘要：

  TAN-1057A-D, dipeptides isolated from bacteria Flexibacter sp. PK-74 and PK-176, are new antibiotics with potent antibacterial activity against methicillin-resistant Staphylococcus aureus. We describe, in detail, the total synthesis of TAN-l057A-D by a convergent route featuring a new method to construct the cyclic amidinourea functional group.

  DOI：

  10.1021/ja972670j

文献信息

• An efficient method for the preparation of amidinoureas
  作者：Chenguang Yuan、Robert M. Williams

  DOI：10.1016/0040-4039(96)00175-x

  日期：1996.3

  A mild and efficient method for the preparation of amidinoureas by reaction of an acyl-S-methylisothiourea with an amine followed by removal of the acyl groups is described.

  描述了通过使酰基-S-甲基异硫脲与胺反应然后除去酰基的温和而有效的制备酰胺基脲的方法。
• Total Synthesis of the Anti Methicillin-Resistant <i>Staphylococcus aureus</i> Peptide Antibiotics TAN-1057A-D
  作者：Chenguang Yuan、Robert M. Williams

  DOI：10.1021/ja972670j

  日期：1997.12.1

  TAN-1057A-D, dipeptides isolated from bacteria Flexibacter sp. PK-74 and PK-176, are new antibiotics with potent antibacterial activity against methicillin-resistant Staphylococcus aureus. We describe, in detail, the total synthesis of TAN-l057A-D by a convergent route featuring a new method to construct the cyclic amidinourea functional group.