N-<2-hydroxy-1,1-bis(hydroxymethyl)ethyl>-N^α-(benzyloxycarbonyl)glycinamide | 91202-74-3

• 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: N-<2-hydroxy-1,1-bis(hydroxymethyl)ethyl>-N^α-(benzyloxycarbonyl)glycinamide
• 英文别名: N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]-N^α-(benzyloxycarbonyl)glycinamide；N^α-benzyloxycarbonyl-N-[tris(hydroxymethyl)methyl]glycinamide；N-[N-(benzyloxycarbonyl)glycyl]tris(hydroxymethyl)aminomethane；N-(benzyloxycarbonyl)glycyl tris(hydroxymethyl)aminomethane；Z-Gly-Tris；benzyl N-[2-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-oxoethyl]carbamate
• CAS: 91202-74-3
• 化学式: C₁₄H₂₀N₂O₆
• 分子量: 312.323
• InChiKey: BWOYDUSFGMHBET-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C
• 沸点：
  675.7±55.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  128
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-<2-hydroxy-1,1-bis(hydroxymethyl)ethyl>-N^α-(benzyloxycarbonyl)glycinamide 在 palladium on activated charcoal calcium sulfate 、 氢气 、 氰化汞 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 28.25h， 生成 Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[5-(2-amino-acetylamino)-2-phenyl-[1,3]dioxan-5-ylmethoxy]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Vesicles and other supramolecular systems made from double-tailed synthetic glycolipids derived from galactosylated tris(hydroxymethyl)aminomethane

  摘要：

  A series of double-tailed hydrocarbon glycolipids derived from tris(hydroxymethyl)aminomethane (Tris) have been prepared. These amphiphiles consist of three parts: a hydrophilic head derived from mono- or polygalactosylated Tris, a linking arm of peptidic nature and a hydrophobic double tail composed of 12 or 18 carbon atom chains. The ability of the new glycolipids to disperse in water, the morphology of the self-assemblies they form and the stability of the latter were shown to depend largely on the volumetric ratio between hydrophilic head and hydrophobic tails. Comparative studies of such substrates allowed a better understanding of the relative role of the various parameters that govern the formation of tubular systems relative to vesicular organizations. In all cases, the introduction of oligomeric galactosylated heads favoured stable vesicular systems over tubules.

  DOI：

  10.1016/0009-3084(95)02475-x
• 作为产物：
  描述：

  Z-甘氨酸-NCA 、 三羟甲基氨基甲烷 以 1,4-二氧六环 、 水 为溶剂， 以51%的产率得到N-<2-hydroxy-1,1-bis(hydroxymethyl)ethyl>-N^α-(benzyloxycarbonyl)glycinamide
  参考文献：
  名称：

  TRIS-脂肪酯衍生物合成中的选择性保护策略

  摘要：

  已经建立了选择性合成具有一个、两个或三个脂肪酯基团的甘氨酰胺三醇 (1) 的亲脂性酰基衍生物的方法。(1)用棕榈酰氯过酰化得到三酰化衍生物。(1) 转化为丙酮化物，然后用棕榈酰氯或月桂酰氯酰化，缩醛水解提供单酰化衍生物。用原乙酸三甲酯处理(1)得到原乙酸衍生物。轻度水解提供单乙酸酯/二醇。两个羟基用棕榈酰氯酰化得到二棕榈酸酯/乙酸酯。乙酸基的选择性裂解得到(1)的二棕榈酸酯。使用原甲酸三甲酯的类似化学通过原甲酸酯、单甲酸酯/二醇和二棕榈酸酯/甲酸酯提供相同的二棕榈酸酯。

  DOI：

  10.1071/ch02124

文献信息

• Synthesis of a Glycolipidic Amphiphilic Nitrone as a New Spin Trap
  作者：Olivier Ouari、Ange Polidori、Bernard Pucci、Paul Tordo、Florence Chalier

  DOI：10.1021/jo982343+

  日期：1999.5.1

  The synthesis of a new amphiphilic nitrone, A, derived from a digalactosyl tris(hydroxymethyl)aminomethane bearing a perfluorocarbon chain is described. A exhibited a surfactant behavior (cmc = 1.6 x 10(-)(5) mol/L), and the specific recognition of the galactosyl moiety grafted on A by the KbCWL1 membrane lectin was established. Preliminary experiments showed that A was able to trap free radicals in

  描述了从带有全氟化碳链的双半乳糖基三（羟甲基）氨基甲烷衍生的新的两亲性腈A的合成。A表现出表面活性剂的行为（cmc ＝ 1.6×10（-）（5）mol / L），并且建立了通过KbCWL1膜凝集素接枝到A上的半乳糖基部分的特异性识别。初步实验表明，A能够捕获水性介质中的自由基，所观察到的ESR光谱的形状很大程度上取决于所捕获自由基的性质。
• Therapeutic compound-fatty acid conjugates
  申请人：Commonwealth Scientific and Industrial Research Organisation

  公开号：US06353124B1

  公开（公告）日：2002-03-05

  The present invention provides therapeutic conjugates which comprise a therapeutic compound bound to one to three acyl groups derived from fatty acids. The therapeutic compounds are preferably non-steroidal anti-infiammatory agents which include a carboxylic acid group. The compounds involve the use of tromethamine or ethanolamine derivative to link the acyl groups derived from fatty acids to the therapeutic compounds.

  本发明提供了治疗性结合物，其中包括一个治疗性化合物与来自脂肪酸的一个至三个酰基结合。这些治疗性化合物通常是非类固醇抗炎药物，包括一个羧酸基团。这些化合物涉及使用醋酸氢三甲胺或乙醇胺衍生物将来自脂肪酸的酰基与治疗性化合物连接起来。
• Total Synthesis of Methotrexate-γ-TRIS-Fatty Acid Conjugates
  作者：C. L. Francis、Q. Yang、N. K. Hart、F. Widmer、M. K. Manthey、H. M. He-Williams

  DOI：10.1071/ch02125

  日期：——

  Several routes for the regiospecific synthesis of lipophilic γ-conjugates of methotrexate are described. Coupling of methotrexate-α-tert-butyl ester with glycyl-TRIS-(mono-/di-/tri-)palmitate followed by trifluoroacetic acid cleavage of the α-protection afforded the target methotrexate-γ-glycyl-TRIS-(mono-/di-/tri-)palmitate derivatives. Methotrexate-α-benzyl-γ-glycyl-TRIS-tripalmitate was prepared

  描述了几种区域特异性合成甲氨蝶呤的亲脂性 γ-缀合物的途径。甲氨蝶呤-α-叔丁酯与甘氨酰-TRIS-(单-/二-/三-)棕榈酸酯偶联，然后用三氟乙酸裂解α-保护，得到目标甲氨蝶呤-γ-甘氨酰-TRIS-(单- /di-/tri-) 棕榈酸酯衍生物。制备了甲氨蝶呤-α-苄基-γ-甘氨酰-TRIS-三棕榈酸酯，但没有发现选择性裂解α-酯的方法。最后连接二氨基蝶啶基甲基部分的方法是成功的，但在最后一步中收率低。4-氨基-4-脱氧-N10-甲基蝶酸与谷氨酰-γ-甘氨酰-TRIS-棕榈酸酯衍生物的偶联有效地提供了所需的缀合物。
• Glycoconjugates of gadolinium complexes for MRI applications
  作者：David A. Fulton、Elisa M. Elemento、Silvio Aime、Linda Chaabane、Mauro Botta、David Parker

  DOI：10.1039/b517997a

  日期：——

  Examples of C-4 symmetric, medium MW conjugates incorporating 12 glucose or galactose groups linked via four dendritic wedges to a central Gd complex have been characterised; their enhanced relaxivity is interpreted in terms of effective motional coupling and large contributions from second sphere water molecules.

  已经表征了包含 12 个葡萄糖或半乳糖基团的 C-4 对称中等分子量缀合物的例子，这些基团通过四个树突楔形物连接到中心 Gd 复合物；它们增强的弛豫性可以用有效的运动耦合和第二球水分子的巨大贡献来解释。
• A Strategy for the Targeting of Photosensitizers. Synthesis, Characterization, and Photobiological Property of Porphyrins Bearing Glycodendrimeric Moieties
  作者：Séverine Ballut、Delphine Naud-Martin、Bernard Loock、Philippe Maillard

  DOI：10.1021/jo102185d

  日期：2011.4.1

  This paper describes the conception, synthesis, and characterization of new tetrapyrrolic chromophores bearing glycodendrimeric moieties inducing a potential increase of tumor targeting by a cluster effect. Two families of monoglycodendrimeric photosensitizers bearing three glycosyl units were designed, prepared with an acceptable overall efficiency and characterized by NMR, UV-visible, and fluorescence spectroscopies. The polarity and log P were evaluated by HPLC and the stir-flask method, respectively. The in vitro photoefficiency against two human tumor cell lines was assessed. The presence of the glycodendrimeric group does not appear to increase the tumor in vitro targeting.