6-O-(3-carboxypropanoyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 119613-87-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 6-O-(3-carboxypropanoyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: 6-O-(3-carboxypropanoyl)-1,2:3,4-di-O-isopropylidene-β-d-galactopyranose；6-O-(3-carboxypropanoyl)-1,2:3,4-di-O-isopropylidene-D-galactopyranose；1,2:3,4-Di-O-isopropylidengalactose-6-succinic monoester
• CAS: 119613-87-5
• 化学式: C₁₆H₂₄O₉
• 分子量: 360.361
• InChiKey: NBVUYOQXEJNVJO-AEOCFKNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-O-(3-carboxypropanoyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 AZT D-galactopyranose-6'-O-succinyl ester
  参考文献：
  名称：

  Synthesis and in vitro chemical and enzymatic stability of glycosyl 3′-azido-3′-deoxythymidine derivatives as potential anti-HIV agents

  摘要：

  New glycosyl derivatives of 3'-azido-3'-deoxythymidine (AZT) (1 and 2) were synthesized in order to improve AZT retention in the blood and to guarantee its sustained release, overcoming the necessity of multiple drug administrations. The esters synthesized (1 and 2) link AZT, by a succinyl linker, to the C-3 position of glucose and to C-6 of galactose. Furthermore, the chemical and enzymatic stabilities of esters 1 and 2 were evaluated in order to determine both their stability in aqueous medium and their feasibility to undergo enzymatic cleavage by esterase to regenerate the original drug. The pharmacokinetic profiles of esters 1 and 2, obtained after systemic administration, showed an interesting controlled release, in particular for ester 2, compared to the pharmacokinetic profile of AZT. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(02)00080-5
• 作为产物：
  描述：

  丁二酸酐 、 双丙酮半乳糖 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以96%的产率得到6-O-(3-carboxypropanoyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  自然化染料：新一类染料的简单直接合成途径——糖偶氮染料 (GAD)

  摘要：

  我们报告了一种通过将合成偶氮染料与乳糖或其单糖成分（半乳糖或葡萄糖）连接来使它们自然化的过程，以提高它们的溶解度，就像许多其他天然染料一样。这种改性使纺织材料的染色过程可以在水中进行，而无需添加表面活性剂或其他添加剂。第一代糖偶氮染料 (GAD) 的合成是通过使用二酯接头将偶氮染料和糖键合来进行的。初步染色测试表明，第一代 GAD 可溶于水，而且这些新染料是多用途的，能够很好地染色不同的织物。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2007）

  DOI：

  10.1002/ejoc.200600686

文献信息

• 基于双分子半乳糖衍生物的水凝胶及其制备方法
  申请人：中北大学

  公开号：CN114195838A

  公开（公告）日：2022-03-18

  本发明公开了一种基于双分子半乳糖衍生物的水凝胶及其制备方法和应用。本发明涉及一种双分子半乳糖衍生物的凝胶因子，其化学式为C26H45N3O16，是由1，2，3，4‑二‑O‑异亚丙基‑α‑D‑吡喃半乳糖、丁二酸酐和3，3’‑二氨基二丙胺溶于氯仿体系中反应，其反应产物与2‑乙氧基‑1‑乙氧碳酰基‑1，2‑二氢喹啉、3，3’‑二氨基二丙胺溶于氯仿体系中制备中间体，中间体在甲醇体系中通过磺酸离子树脂柱制备得到。本发明所述的凝胶因子可以在水中形成稳定的凝胶。经测试，本发明制备的水凝胶具有良好的热稳定性、耐酸性、耐碱性，其在化学、生物、医学等领域具有广阔的应用前景。
• NG-Acyl-argininamides as NPY Y1 receptor antagonists: Influence of structurally diverse acyl substituents on stability and affinity
  作者：Stefan Weiss、Max Keller、Günther Bernhardt、Armin Buschauer、Burkhard König

  DOI：10.1016/j.bmc.2010.07.028

  日期：2010.9

  N-G-Acylated argininamides, covering a broad range of lipophilicity (calculated log D values: -1.8-12.5), were synthesized and investigated for NPY Y-1 receptor (Y1R) antagonism, Y1R affinity and stability in buffer (N-G-deacylation, yielding BIBP 3226). Broad structural variation of substituents was tolerated. The K-i (binding) and K-b values (Y1R antagonism) varied from low nM to one-digit mu M. Most of the compounds proved to be sufficiently stable at pH 7.4 over 90 min to determine reliable pharmacological data in vitro. Exceptionally high instability was detected when a succinyl moiety was attached to the guanidine, probably, due to an intramolecular cleavage mechanism. (C) 2010 Elsevier Ltd. All rights reserved.
• Colouring agent containing a mono- or disaccharide
  申请人：Universita Degli Studi di Firenze

  公开号：EP1462484B1

  公开（公告）日：2008-07-02
• ‘Naturalization’ of textile disperse dyes through glycoconjugation: the case of a bis(2-hydroxyethyl) group containing azo dye
  作者：Roberto Bianchini、Giorgio Catelani、Riccardo Cecconi、Felicia D’Andrea、Elena Frino、Jalal Isaad、Massimo Rolla

  DOI：10.1016/j.carres.2008.02.009

  日期：2008.8

  A family of five strictly related glycoconjugated azo dyes (GADs), characterized by the presence of the same chromophore and a variable number (1-4) of deprotected hexose units, has been prepared by employing succinate bridges for connecting the azo dye and the sugar portions. The modulation of the hydrophilic portion determines the appreciable changes in the water solubility of GADs. In all the cases, however, hydrophobic fibres (polyester) were homogeneously dyed with GADs at temperatures lower than that used for original azo dyes, at atmospheric pressure, and avoiding the use of surfactants. Furthermore, GADs show an interesting multipurpose character leading to dyeing well also the natural fibres as, for instance, wool. The presence of a variable number of hexose units in the different GADs determines some changes in the colour intensity of dyed fabrics, but in all the cases an appreciable rubbing and water fastness were maintained. (C) 2008 Elsevier Ltd. All rights reserved.