N[((2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl bishydroxymethyl)methyl]acrylamide | 170124-49-9

• 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',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl bishydroxymethyl)methyl]acrylamide
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-hydroxy-2-(hydroxymethyl)-2-(prop-2-enoylamino)propoxy]oxan-2-yl]methyl acetate
• CAS: 170124-49-9
• 化学式: C₂₁H₃₁NO₁₃
• 分子量: 505.476
• InChiKey: IQVXHGTXJUNVFZ-DABHTEOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  193
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N[((2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl bishydroxymethyl)methyl]acrylamide 在 甲醇 、 sodium methylate 作用下， 以 甲苯 为溶剂， 生成 bis[(N-(3-perfluorohexyl)ethylcarboxamide)oxymethyl]-O-(β-D-galactopyranosyl)oxymethyl N-acrylamidomethane
  参考文献：
  名称：

  衍生自Tris的可聚合双链糖脂的合成。在水性介质中聚合。胶体行为的初步研究

  摘要：

  制备了一系列衍生自三（羟甲基）氨基甲烷并在亲水头上带有丙烯酰基部分的单尾和双尾氢和全氟化碳表面活性剂。通过超声处理分散在水中的双水合表面活性剂形成囊泡，该囊泡在紫外线照射后沉淀。我们描述了一种通过添加单壳两亲物来稳定聚合过程中稳定这些水泡分散体的新方法。©1997由Elsevier Science Ltd发布。

  DOI：

  10.1016/s0040-4039(97)00413-9
• 作为产物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(5-acryloylamino-2-phenyl-[1,3]dioxan-5-ylmethoxy)-tetrahydro-pyran-4-yl ester 在 溶剂黄146 作用下， 以100%的产率得到N[((2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl bishydroxymethyl)methyl]acrylamide
  参考文献：
  名称：

  Synthèse de glycolipides polymérisables Dérivés du Tris(hydroxyméthyl)aminométhane: Préparation de micelles polymérisées.

  摘要：

  We have synthesized a series of new polymerizable glycolipids derived from Tris(hydroxymethyl) aminomethane (TRIS). Galactosylation of TRIS was performed in good yield by means of ultrasounds. Polymerization of 11-N-acrylamido-N-Tris(beta-D-galactopyranosyl oxymethyl)methyl undecanamide in aqueous solution by UV irradiation, led to polymerized micellar structures (A).

  DOI：

  10.1016/s0040-4039(00)60523-3

文献信息

• Synthesis and Preliminary Assessments of Ethyl-Terminated Perfluoroalkyl Nonionic Surfactants Derived from Tris(hydroxymethyl)acrylamidomethane
  作者：Philippe Barthélémy、Bruno Ameduri、Elodie Chabaud、Jean-Luc Popot、Bernard Pucci

  DOI：10.1021/ol990558f

  日期：1999.12.1

  describe the synthesis and preliminary physicochemical and biological assessments of a new class of nonionic hybrid hydrofluoro amphiphiles derived from tris(hydroxymethyl)aminomethane (THAM). The synthesis of the hydrophobic tail of these amphiphiles is based on the preparation of an asymmetrical hydrofluorocarbon derivative containing an ethyl segment, a fluorocarbon core, and an ethyl thiol moiety. This

  我们描述了从三（羟甲基）氨基甲烷（THAM）派生的一类新的非离子杂化氢氟两亲物的合成以及初步的理化和生物学评估。这些两亲物的疏水尾的合成是基于制备不对称的氢氟烃衍生物，该衍生物包含乙基链段，碳氟化合物核和乙基硫醇部分。该分子导致THAM半乳糖基化的单加合物或端粒。这些两亲物既不显示对细胞膜的去污力，也不显示膜蛋白变性。
• Stabilization of polymerized vesicular systems: an application of the dynamic molecular shape concept
  作者：Michel Wathier、Ange Polidori、Karine Ruiz、Anne-Sylvie Fabiano、Bernard Pucci

  DOI：10.1016/s0009-3084(02)00006-3

  日期：2002.5

  A series of glycolipid surfactants derived from Tris(hydroxymethyl)acrylamidomethane (THAM) and bearing hydrocarbon or perfluorocarbon tails and an acryloyl group attached to their polar head was prepared to explore the aqueous behavior of the supramolecular systems they form. The dispersion Of surfactants was achieved in water under ultrasonication conditions. Hydrocarbon Compounds give heterogeneous vesicular assemblies. In the case of perfluorocarbon derivatives homogeneous vesicles were obtained. However after Way storage, all these systems fuse. To stabilize these vesicles, polymerization by ultra violet (UV) irradiation was carried Out. During this reaction, a precipitation in water was observed for the hydrocarbon surfactants, whereas fluorocarbon Structures provide stable vesicles Without any alteration of their size. According to these results, the polymerization process was achieved, in the case of hydrocarbon glycolipid, in the presence of different cosurfactants bearing a single hydrocarbon tail or a polyhydroxylated head and a cholesterol terminus. In Such conditions, homogeneous stable vesicles were prepared. Moreover, the THAM derived telomers bearing a cholesterol terminus were able to stabilize and reduce the size of vesicles formed with synthetic glycolipid surfactants. The drug encapsulation ability of these systems was investigated by measurement of the release kinetics of a fluorescent dye, carboxyfluorescein (CF), before and after polymerization. (C) 2002 Published by Elsevier Science Ireland Ltd.
• A new class of sulfoxide surfactants derived from Tris. Synthesis and preliminary assessments of their properties
  作者：Philippe Barthélémy、Jean Claude Maurizis、Jean Michel Lacombe、Bernard Pucci

  DOI：10.1016/s0960-894x(98)00263-7

  日期：1998.6

  A new class of non-ionic amphiphilic molecules suitable for biological purposes, especially extraction of membrane proteins, is reported. Such surfactants were prepared in two steps : addition of alkyl or fluoroalkyl mercaptan on Tris(hydroxymethyl)acrylamidomethane (THAM) derivatives, followed by the oxydation of sulfide group in sulfoxide moiety in order to provide water solubility to the molecule. The detergent efficiency of these new surfactants were assayed on rat liver cells. (C) 1998 Elsevier Science Ltd. All nights reserved.