(4R,3'R,2'R)-3-<2'-bromo-3'-hydroxy-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl>-4-isopropyl-2-oxazolidinone | 121895-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (4R,3'R,2'R)-3-<2'-bromo-3'-hydroxy-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl>-4-isopropyl-2-oxazolidinone
• 英文别名: (4R)-3-[(2R,3S)-2-bromo-3-hydroxy-3-(1-tritylimidazol-4-yl)propanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 121895-45-2
• 化学式: C₃₁H₃₀BrN₃O₄
• 分子量: 588.501
• InChiKey: SJZASGGBHHZHSO-IARZGTGTSA-N

物化性质

• 熔点：
  116.5-118.5 °C (decomp)
• 沸点：
  712.0±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,3'R,2'R)-3-<2'-bromo-3'-hydroxy-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl>-4-isopropyl-2-oxazolidinone 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 以85%的产率得到(2'S,3'R,4R)-3-[2'-azido-3'-hydroxy-3'-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl]-4-isopropyl-2-oxazolidinone
  参考文献：
  名称：

  An Efficient Synthesis oferythro-β-Hydroxy-L-histidine, the Pivotal Amino Acid of Bleomycin-Fe(II)–O₂Complex

  摘要：

  (R)-3-bromoacetyl-4-isopropyl-1,3-oxazolidin-2-one 与 1-triphenylmethylimidazole-4-carbaldehyde 发生醛醇反应，然后与 LiN3 发生 SN2 反应并加氢，在有机溶剂中高效合成了赤式-β-羟基-l-组氨酸。

  DOI：

  10.1246/cl.1988.1873
• 作为产物：
  描述：

  (R)-3-溴乙酰基-4-异丙基-1,3-恶唑烷-2-酮 、 1-三苯甲基咪唑-4-甲醛 在 三氟甲磺酸二丁硼 、 三乙胺 作用下， 生成 (4R,3'R,2'R)-3-<2'-bromo-3'-hydroxy-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl>-4-isopropyl-2-oxazolidinone
  参考文献：
  名称：

  An Efficient Synthesis oferythro-β-Hydroxy-L-histidine, the Pivotal Amino Acid of Bleomycin-Fe(II)–O₂Complex

  摘要：

  (R)-3-bromoacetyl-4-isopropyl-1,3-oxazolidin-2-one 与 1-triphenylmethylimidazole-4-carbaldehyde 发生醛醇反应，然后与 LiN3 发生 SN2 反应并加氢，在有机溶剂中高效合成了赤式-β-羟基-l-组氨酸。

  DOI：

  10.1246/cl.1988.1873

文献信息

• Otsuka, Masami; Nishio, Toshiyuki; Oshitari, Tetsuta, Heterocycles, 1992, vol. 33, # 1, p. 27 - 34
  作者：Otsuka, Masami、Nishio, Toshiyuki、Oshitari, Tetsuta、Owa, Takashi、Sugiura, Yukio、et al.

  DOI：——

  日期：——
• OWA, TAKASHI;OTSUKA, MASAMI;OHNO, MASAJI, CHEM. LETT.,(1988) N1, C. 1873-1874
  作者：OWA, TAKASHI、OTSUKA, MASAMI、OHNO, MASAJI

  DOI：——

  日期：——
• Total Synthesis of Bleomycin A2 and Related Agents. 1. Synthesis and DNA Binding Properties of the Extended C-Terminus: Tripeptide S, Tetrapeptide S, Pentapeptide S, and Related Agents
  作者：Dale L. Boger、Steven L. Colletti、Takeshi Honda、Royce F. Menezes

  DOI：10.1021/ja00092a011

  日期：1994.6

  Full details of concise, diastereocontrolled syntheses of 2-5 and their incorporation into tri-, tetra-, and pentapeptide S, the C-terminus of bleomycin Alt are described. The extension of the studies to the synthesis of a complete set of tri- and tetrapeptide S structural analogs 29a,b and 43b-j is detailed, and their DNA binding constants (apparent K-B, calf thymus DNA) and apparent binding site sizes were determined. Consistent with past observations, the studies highlight the fact that the majority of the DNA binding affinity for bleomycin A(2) (1.0 X 10(5) M(-1)) and deglycobleomycin Aa (1.1 x 10(5) M(-1)) is embodied within N-BOC-tripeptide S (0.26 X 10(5) M(-1)). The additional comparisons of 29a (O.18 x 10(5) M(-1)), N-BOC-tetrapeptide S (0.21 x 10(5) M(-1)), 43h (0.20 x 10(5) M(-1)), and N-BOC-pentapeptide S (0.23 X 10(5) M(-1)) versus N-BOC-dipeptide S (0.10 x 10(5) M(-1)) indicate productive stabilizing binding interactions for the tripeptide S L-threonine subunit and substituent, illustrate that the entire pentanoic acid subunit of tetrapeptide S and its substituents do not significantly contribute to DNA binding affinity, and indicate that the entire beta-hydroxy-L-histidine subunit of pentapeptide S does not contribute to DNA binding affinity. With the exception of the L-threonine side chain substituent, the observations suggest that the tri- and tetrapeptide S substituent effects on the bleomycin A(2) DNA cleavage reaction are not due to substantial stabilizing binding interactions with duplex DNA. In addition, the measured apparent binding site sizes for bleomycin A(2)(3.8 base pairs), deglycobleomycin A(2) (3.9 base pairs), N-BOC-tripeptide S (3.6 base pairs), N-BOC-tetrapeptide S (3.7 base pairs), 43h (3.5 base pairs), and N-BOC-pentapeptide S (4.2 base pairs) versus N-BOC-dipeptide S (2.2 base pairs) and 29a (2.7 base pairs) suggest that it is the tripeptide S subunit of bleomycin A(2) that is fully bound to duplex DNA, that the tripeptide S L-threonine hydroxyethyl substituent detectably affects the agent interaction with duplex DNA, but that the presence or absence of the other tetrapeptide S and pentapeptide S backbone substituents do not substantially alter the binding site size or tripeptide S binding mode.
• An Efficient Synthesis of<i>erythro</i>-β-Hydroxy-L-histidine, the Pivotal Amino Acid of Bleomycin-Fe(II)–O₂Complex
  作者：Takashi Owa、Masami Otsuka、Masaji Ohno

  DOI：10.1246/cl.1988.1873

  日期：1988.11.5

  erythro-β-Hydroxy-l-histidine is efficiently synthesized in organic solvents from the aldol reaction of (R)-3-bromoacetyl-4-isopropyl-1,3-oxazolidin-2-one and 1-triphenylmethylimidazole-4-carbaldehyde followed by SN2 reaction with LiN3 and hydrogenation.

  (R)-3-bromoacetyl-4-isopropyl-1,3-oxazolidin-2-one 与 1-triphenylmethylimidazole-4-carbaldehyde 发生醛醇反应，然后与 LiN3 发生 SN2 反应并加氢，在有机溶剂中高效合成了赤式-β-羟基-l-组氨酸。