(2S,3S,4R)-1-(6-deoxy-6-amino)-α-D-galactopyranosyloxy-2-hexacosanoylamino-3,4-octadecandiol | 424823-18-7

• 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-amino)-α-D-galactopyranosyloxy-2-hexacosanoylamino-3,4-octadecandiol
• 英文别名: (2S,3S,4R)-1-O-(6-amine-α-D-galactopyranosyl)-D-ribo-2-hexacosanoylamino-1,3,4-octadecantriol；(2S,3S,4R)-1-(6-amino-6-deoxy-α-D-galactopyranosyloxy)-2-hexacosanoylamido-octadecane-3,4-diol；(2S,3S,4R)-1-O-(6-deoxy-6-amino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol；"N-[(1S,2S,3R)-1-[[(6-Amino-6-deoxy-alpha-D-galactopyranosyl)oxy]methyl]-2,3-dihydroxyheptadecyl]hexacosanamide"；N-[(2S,3S,4R)-1-[(2S,3R,4S,5R,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4-dihydroxyoctadecan-2-yl]hexacosanamide
• CAS: 424823-18-7
• 化学式: C₅₀H₁₀₀N₂O₈
• 分子量: 857.353
• InChiKey: VDRCODVEURZCQH-BYSUZVQFSA-N

物化性质

• 沸点：
  935.2±65.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  60
• 可旋转键数：
  44
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  175
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (+)生物素-N-琥珀酰亚胺基酯 、 (2S,3S,4R)-1-(6-deoxy-6-amino)-α-D-galactopyranosyloxy-2-hexacosanoylamino-3,4-octadecandiol 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以52%的产率得到
  参考文献：
  名称：

  荧光团和生物素附加的6“-氨基-6”-脱氧半乳糖基神经酰胺的合成和NKT细胞刺激特性。

  摘要：

  α-半乳糖基神经酰胺是人类T细胞的有效刺激剂。通过CD1d结合糖脂，将其呈递给T细胞并形成CD1d-糖脂-T细胞受体复合物来进行刺激。为了便于阐明T细胞刺激所必需的糖脂的结构特征，已经制备了在糖的C6位置附加了小分子的α-半乳糖基神经酰胺。附加的分子不会显着影响糖脂刺激T细胞的能力。[反应：看文字]

  DOI：

  10.1021/ol025565+
• 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 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 27.41h， 生成 (2S,3S,4R)-1-(6-deoxy-6-amino)-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

• NOVEL alpha-GALACTOSYL CERAMIDE ANALOGS AND USES THEREOF
  申请人：Chang Gung Memorial Hospital, Linkou

  公开号：US20160115188A1

  公开（公告）日：2016-04-28

  The present invention is directed to compounds of formula (I) and pharmaceutical compositions comprising compounds of formula (I) and pharmaceutically acceptable carriers. The invention further comprises improved process for the preparation of compounds of formula (I), and the use of compound of formula (I) to induce a specific immune response or to treat an autoimmune disease.

  本发明涉及化合物的公式(I)以及包含公式(I)化合物和药用载体的药物组合物。该发明还涉及改进的用于制备公式(I)化合物的方法，以及利用公式(I)化合物诱导特定免疫反应或治疗自身免疫疾病的用途。
• 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] 6"-AMINO-6"-DEOXYGALACTOSYLCERAMIDES<br/>[FR] 6"-AMINO-6"-DEOXYGALACTOSYLCERAMIDES
  申请人：UNIV BRIGHAM YOUNG

  公开号：WO2004094444A1

  公开（公告）日：2004-11-04

  This invention relates to galactosylceramide compounds.

  这项发明涉及半乳糖鞘氨醇化合物。
• [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。
• An efficient synthesis of a 6″-BODIPY-α-Galactosylceramide probe for monitoring α-Galactosylceramide uptake by cells
  作者：Janice M.H. Cheng、Stephanie H. Chee、Yusuf Dölen、Martijn Verdoes、Mattie S.M. Timmer、Bridget L. Stocker

  DOI：10.1016/j.carres.2019.107840

  日期：2019.12

  Herein, an efficient synthesis of BODIPY-α-Galactosylceramide 3, which can be used to study the cellular uptake of the potent immunostimulatory parent compound α-Galactosylceramide, is reported. Key in our synthetic strategy is the six-step synthesis of the core BODIPY scaffold (64% yield overall) and its quantitative conversion to an N-hydroxysuccinimidyl ester to facilitate conjugation and purification of the target glycolipid. For the preparation of the core of the glycolipid, the solubility of the lipid acceptor proved to be critical. The ability of BODIPY-αGalCer 3 to activate invariant natural killer cells was then demonstrated in vitro.