2-二(叔-丁基氧羰基)-L-高丝氨酸叔-丁酯 | 945744-04-7

• 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
• 中文名称: 2-二(叔-丁基氧羰基)-L-高丝氨酸叔-丁酯
• 英文名称: tert-butyl N,N-bis(tert-butyloxycarbonyl)-L-homoserinate
• 英文别名: tert-butyl (S)-2-bis(tert-butoxycarbonyl)amino-4-hydroxybutanoate；tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-4-hydroxy-butanoate；tert-butyl 2-(S)-2-[bis(tert-butoxycarbonyl)amino]-4-hydroxybutanoate；2-Di(tert-butyloxycarbonyl)-L-homoserine tert-Butyl Ester；tert-butyl (2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-4-hydroxybutanoate
• CAS: 945744-04-7
• 化学式: C₁₈H₃₃NO₇
• 分子量: 375.463
• InChiKey: OOJGLSISAHOXOW-LBPRGKRZSA-N

物化性质

• 沸点：
  443.6±55.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-二(叔-丁基氧羰基)-L-高丝氨酸叔-丁酯 在 dipyridine chromium trioxide 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到tert-butyl L-2-[bis(tert-butoxycarbonyl)amino]-4-oxo-butanoate
  参考文献：
  名称：

  Asymmetric synthesis of differentially protected meso-2,6-diaminopimelic acid

  摘要：

  meso-2,6-Diaminopimelic acid, an important linking component of bacterial cell walls and a biosynthetic precursor of L-lysine has been prepared differentially protected in a stereospecific manner from both L-aspartic and L-glutamic acid. The key step to establish the second chiral center involves the asymmetric reduction of a pyruvate moiety with Alpine-Borane(R). S-2-Amino-6-oxopimelic acid, the hydrolyzed open chain form of tetrahydrodipicolinic acid, a biosynthetic precursor of meso-2,6-diaminopimelic acid, was also prepared via deprotection of the key pyruvate intermediate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01844-0
• 作为产物：
  描述：

  1-tert-butyl 4-methyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}butanedioate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 以98%的产率得到2-二(叔-丁基氧羰基)-L-高丝氨酸叔-丁酯
  参考文献：
  名称：

  An unexpected product from attempted reductive etherification of a silyl alcohol with an aldehyde

  摘要：

  Reductive etherification, using BiBr3/Et3SiH, between two modified amino acids, one with a silyl alcohol side chain and one with an aldehyde side chain, gave, not the desired bis-amino acid, but a tetrahydrooxazine, in good yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.163

文献信息

• [EN] INHIBITORS OF DNMT1 AS ANTICANCER THERAPEUTIC AGENTS<br/>[FR] INHIBITEURS DE DNMT1 UTILISÉS EN TANT QU'AGENTS THÉRAPEUTIQUES ANTICANCÉREUX
  申请人：VICTORIA LINK LTD

  公开号：WO2020013712A1

  公开（公告）日：2020-01-16

  Inhibitors of DNA methyltransferase 1 (an enzyme responsible for the maintenance of DNA CpG methylation marks in human cells) and their use as therapeutic agents against various cancers. The invention relates to compounds, pharmaceutical compositions, methods for inhibiting DNA methyltransferase 1, and methods for treating cancer. The inhibitors are compounds of the general formula.

  DNA 甲基转移酶 1 的抑制剂（一种负责在人类细胞中维持 DNA CpG 甲基化标记的酶）及其作为治疗各种癌症的药物的使用。该发明涉及化合物、药物组合物、抑制 DNA 甲基转移酶 1 的方法以及治疗癌症的方法。这些抑制剂是一般公式的化合物。
• Synthesis and Characterization of Transition-State Analogue Inhibitors against Human DNA Methyltransferase 1
  作者：Farah Lamiable-Oulaidi、Rajesh K. Harijan、Karl J. Shaffer、Douglas R. Crump、Yan Sun、Quan Du、Shivali A. Gulab、Ashna A. Khan、Andreas Luxenburger、Anthony D. Woolhouse、Simone Sidoli、Peter C. Tyler、Vern L. Schramm

  DOI：10.1021/acs.jmedchem.1c01869

  日期：2022.4.14

  methyltransferase 1 (DNMT1) silences tumor-suppression genes, and inhibition of DNMT1 can reactivate silenced genes. The 5-azacytidines are approved inhibitors of DNMT1, but their mutagenic mechanism limits their utility. A synthon approach from the analogues of S-adenosylhomocysteine, methionine, and deoxycytidine recapitulated the chemical features of the DNMT1 transition state in the synthesis of 16 chemically

  人类 DNA 甲基转移酶 1 (DNMT1) 对 CpG 区域的高甲基化使肿瘤抑制基因沉默，而对 DNMT1 的抑制可以重新激活沉默的基因。5-氮杂胞苷是经批准的 DNMT1 抑制剂，但它们的诱变机制限制了它们的效用。来自S-腺苷高半胱氨酸、蛋氨酸和脱氧胞苷类似物的合成子方法在 16 种化学稳定的过渡态模拟物的合成中概括了 DNMT1 过渡态的化学特征。对引起纯化的DNMT1的完全和部分抑制的抑制剂进行了表征。抑制剂对 DNMT1 与 DNMT3b 显示出适度的选择性。活性位点对接预测抑制剂与S-腺苷-l的相互作用催化位点的甲硫氨酸和脱氧胞苷区域，通过直接结合分析进行验证。纯化的 DNMT1 的抑制剂作用未反映在培养的细胞中。部分抑制剂激活细胞 DNA 甲基化，而完全抑制剂对细胞 DNA 甲基化没有影响。这些化合物提供了对用于 DNA 甲基转移酶的新的非共价 DNMT 化学支架家族的化学访问。
• [60]Fullerene <scp>l</scp>-Amino Acids and Peptides: Synthesis under Phase-Transfer Catalysis Using a Phosphine–Borane Linker. Electrochemical Behavior
  作者：Pauline Minois、Jérôme Bayardon、Rita Meunier-Prest、Sylvain Jugé

  DOI：10.1021/acs.joc.7b01737

  日期：2017.11.3

  yields. Finally, the hydrophosphination reaction of [60]fullerene by the sec-phosphine borane compounds was performed under PTC to obtain C60-amino acid or dipeptide derivatives in yields up to 80% by P–C bond formation. This addition reaction which proceeds in mild and moderate dilute conditions (0.03 M) leads to [60]fullerene derivatives as epimeric mixtures (∼1:1) due to the P-chirogenic center but

  描述了一种将氨基酸和肽衍生物连接到[60]富勒烯的新方法。它与仲膦硼烷一起使用氢磷酸化。首先，通过在相转移催化（PTC）下用γ-碘-α-氨基酯试剂将苯基膦硼烷烷基化，从而实现了二级膦硼烷仲氨基酸衍生物的立体选择性合成。其次，将仲膦硼烷氨基酯皂化并与α，γ-二氨基酯偶联，以高收率得到相应的二肽衍生物。最后，在PTC下进行仲膦硼烷化合物与[60]富勒烯的加氢磷酸反应，得到C 60。-氨基酸或二肽衍生物通过P–C键形成的产率高达80％。这种在轻度和中度稀薄条件下（0.03 M）进行的加成反应由于P-色原中心而导致[60]富勒烯衍生物为差向异构体混合物（〜1：1），但氨基酸或肽部分未消旋。此外，在控制电位电解后，通过循环伏安法和光谱电化学研究了C 60膦硼烷硼酸酯的电化学行为。它显示了逆式加氢磷酸反应生成游离的[60]富勒烯和仲膦硼烷氨基酯化合物的证据。因此，秒的合成-膦硼烷氨基酸，随后在相转移催
• An unexpected product from attempted reductive etherification of a silyl alcohol with an aldehyde
  作者：Christopher G.H. White、Alethea B. Tabor

  DOI：10.1016/j.tet.2007.03.163

  日期：2007.7

  Reductive etherification, using BiBr3/Et3SiH, between two modified amino acids, one with a silyl alcohol side chain and one with an aldehyde side chain, gave, not the desired bis-amino acid, but a tetrahydrooxazine, in good yield. (c) 2007 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of differentially protected meso-2,6-diaminopimelic acid
  作者：John L. Roberts、Cecil Chan

  DOI：10.1016/s0040-4039(02)01844-0

  日期：2002.10

  meso-2,6-Diaminopimelic acid, an important linking component of bacterial cell walls and a biosynthetic precursor of L-lysine has been prepared differentially protected in a stereospecific manner from both L-aspartic and L-glutamic acid. The key step to establish the second chiral center involves the asymmetric reduction of a pyruvate moiety with Alpine-Borane(R). S-2-Amino-6-oxopimelic acid, the hydrolyzed open chain form of tetrahydrodipicolinic acid, a biosynthetic precursor of meso-2,6-diaminopimelic acid, was also prepared via deprotection of the key pyruvate intermediate. (C) 2002 Elsevier Science Ltd. All rights reserved.