(2S,3S,4R)-1-(6-deoxy-6-azido-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol | 1260236-41-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,4R)-1-(6-deoxy-6-azido-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol
• 英文别名: (2S,3S,4R)-1-O-(6-deoxy-6-azido-α-D-galactopyranosyl)-2-hexacosanoylamino-1,3,4-octadecanetriol；6-deoxy-6-azido-α-galactosylceramide；(2S,3S,4R)-1-O-(6-deoxy-6-azido-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol；N-[(2S,3S,4R)-1-[(2S,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4-dihydroxyoctadecan-2-yl]hexacosanamide
• CAS: 1260236-41-6
• 化学式: C₅₀H₉₈N₄O₈
• 分子量: 883.35
• InChiKey: JGDQTOKAQZCOPA-BYSUZVQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  62
• 可旋转键数：
  45
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  163
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-1-(6-deoxy-6-azido-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol 在 三甲基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.08h， 生成 1-O-(6-benzureido-6-deoxy-α-D-galactopyranosyl)-2-hexacosylamino-1,3,4-octadecanetriol
  参考文献：
  名称：

  Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids

  摘要：

  A concise route to the 6-azido-6-deoxy-alpha-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized alpha-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach.

  DOI：

  10.1021/jo102064p
• 作为产物：
  描述：

  糖脂 在 2,6-二甲基吡啶 、 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 sodium acetate 、 四丁基碘化铵 、 氟化氢吡啶 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 21.41h， 生成 (2S,3S,4R)-1-(6-deoxy-6-azido-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol
  参考文献：
  名称：

  Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids

  摘要：

  A concise route to the 6-azido-6-deoxy-alpha-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized alpha-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach.

  DOI：

  10.1021/jo102064p

文献信息

• Towards multivalent CD1d ligands: synthesis and biological activity of homodimeric α-galactosyl ceramide analogues
  作者：Peter J. Jervis、Marie Moulis、John-Paul Jukes、Hemza Ghadbane、Liam R. Cox、Vincenzo Cerundolo、Gurdyal S. Besra

  DOI：10.1016/j.carres.2012.02.034

  日期：2012.7

  Graphical abstract

  图形概要
• Rapid access to 6″-functionalized α-galactosyl ceramides by using 2-naphthylmethyl ether as the permanent protecting group
  作者：Yichu Liu、Xiaoyan Xu、Qi Gao、Shiqiang Yan、Yingxia Li、Ning Ding

  DOI：10.1016/j.bmcl.2017.02.055

  日期：2017.4

  strategy for the synthesis of 6″-functionalized α-GalCers by using NAP ether group for permanent hydroxyl protection was developed, which provide the flexibility necessary for the incorporation of a wide range of functional groups in target molecules including alkyne, azide, thiol that are intolerant to Pd-catalyzed hydrogenolysis as well as other functionalities like carboxylic acid and amine. This strategy

  通过使用NAP醚基团进行永久羟基保护，开发了一种用于合成6''-官能化α-GalCers的通用策略，该策略提供了将各种官能团掺入目标分子（包括炔烃，叠氮化物，硫醇）所需的灵活性不耐Pd催化的氢解以及其他功能（如羧酸和胺）的金属。该策略也适用于其他糖缀合物合成，尤其是那些包含可点击标签和不饱和官能团的糖缀合物。
• [EN] AMINO SPHINGOGLYCOLIPID ANALOGUES<br/>[FR] ANALOGUES D'AMINO-SPHINGOGLYCOLIPIDE
  申请人：ANDERSON REGAN JAMES

  公开号：WO2015187040A1

  公开（公告）日：2015-12-10

  The invention relates to amino sphingoglycolipid analogues and peptide derivatives thereof, compositions comprising these compounds and methods of treating or preventing diseases or conditions using such compounds, especially diseases or conditions relating to cancer, infection, atopic disorders, autoimmune disease or diabetes.

  该发明涉及氨基鞘糖脂类似物及其肽衍生物，包括这些化合物的组合物以及使用这些化合物治疗或预防疾病或病况的方法，特别是涉及癌症、感染、特应性疾病、自身免疫疾病或糖尿病等疾病或病况。
• New CD1d agonists: Synthesis and biological activity of 6″-triazole-substituted α-galactosyl ceramides
  作者：Peter J. Jervis、Lisa M. Graham、Erin L. Foster、Liam R. Cox、Steven A. Porcelli、Gurdyal S. Besra

  DOI：10.1016/j.bmcl.2012.05.009

  日期：2012.7

  Huisgen [3+2] dipolar cycloaddition of 6 ''-azido-6 ''-deoxy-alpha-galactosyl ceramide 11 with a range of alkynes (or a benzyne precursor) yielded a series of triazole-containing alpha-galactosyl ceramide (alpha-GalCer) analogues in high yield. These alpha-GalCer analogues and the precursor azide 11 were tested for their ability to activate iNKT cells and stimulate IL-2 cytokine secretion in vitro, and IFN-gamma and IL-4 cytokine secretion in vivo. Some of these analogues, specifically 11, 12b, 12f and 13, were more potent IL-2 stimulators than the prototypical CD1d agonist, alpha-GalCer 1. In terms of any cytokine bias, most of the triazole-containing analogues exhibited a small Th2 cytokine-biasing response relative to that shown by alpha-GalCer 1. In contrast, the cycloaddition precursor, namely azide 11, provided a small Th1 cytokine-biasing response. (C) 2012 Elsevier Ltd. All rights reserved.
• [EN] IMMUNOSTIMULATORY COMPOSITIONS<br/>[FR] COMPOSITIONS IMMUNOSTIMULANTES
  申请人：[en]VICTORIA LINK LIMITED

  公开号：WO2023121483A1

  公开（公告）日：2023-06-29

  The present application is directed to immunomodulatory compositions comprising invariant NKT cell (iNKT cell) agonist compounds that induce expansion of tissue resident memory T-cells (Trm Cells) in combination with an immune stimulator agent that enhances an immune response to a target antigen or a polynucleotide encoding the immune stimulator. The iNKT agonists are a-GalCer analogue compounds modified at the 6 position of the galactose ring. The immune stimulator is an antigen or an mRNA encoding an antigen to create a vaccine formulation. These combinations are used in the treatment of infection or cancer in a subject, or to enrich the number of Trm cells in the liver of a subject.