2-azido-3,4-O-isopropylidene-D-ribo-1,3,4-octanetriol | 745041-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-3,4-O-isopropylidene-D-ribo-1,3,4-octanetriol
• 英文别名: (2S)-2-azido-2-[(4S,5R)-5-butyl-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 745041-57-0
• 化学式: C₁₁H₂₁N₃O₃
• 分子量: 243.306
• InChiKey: MOZRANJBIDNQAH-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-azido-3,4-O-isopropylidene-D-ribo-1,3,4-octanetriol 在 Lindlar's catalyst 四丁基溴化铵 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 N-((S)-1-((4S,5R)-5-butyl-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)tetracosanamide
  参考文献：
  名称：

  Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs

  摘要：

  Analogs of immunomodulatory glycolipid OCH (2) were prepared and minimum structure requirement to exhibit equivalent profiles was disclosed. Analogs bearing non-linear hydrocarbon chain in the phytosphingosine moiety (18, 19) were shown for the first time to possess comparable cytokine inducing profile to 2. Molecular modeling of 2/hCD1d complex based on the crystal structure of alpha-GalCer (1)/hCDld complex is also described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.081
• 作为产物：
  描述：

  在 吡啶 、 sodium azide 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-azido-3,4-O-isopropylidene-D-ribo-1,3,4-octanetriol
  参考文献：
  名称：

  Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs

  摘要：

  Analogs of immunomodulatory glycolipid OCH (2) were prepared and minimum structure requirement to exhibit equivalent profiles was disclosed. Analogs bearing non-linear hydrocarbon chain in the phytosphingosine moiety (18, 19) were shown for the first time to possess comparable cytokine inducing profile to 2. Molecular modeling of 2/hCD1d complex based on the crystal structure of alpha-GalCer (1)/hCDld complex is also described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.081

文献信息

• Synthesis and Bioassay of Neurogenically Potent Gangliosides DSG-A, Hp-s1 and Their Analogues
  作者：Ganesh B. Shelke、Yu-Hsuan Lih、Ying-Ju Liao、Chih-Wu Liang、Tzer-Min Kuo、Ying-Chin Ko、Shun-Yuan Luo

  DOI：10.1021/acschemneuro.8b00055

  日期：2018.6.20

  the search of a potent candidate for neurotherapy, we designed and synthesized various analogues of ganglioside Hp-s1. The modification includes the change in hydrophobicity by varying the carbon chain length, altering the number of hydrogen bonds, and replacing the anomeric atom. The chemical synthesis was carried out by using various methods and discussed in details. The neuritogenic activities of

  为了寻找有效的神经疗法候选人，我们设计并合成了神经节苷脂Hp-s1的各种类似物。所述修饰包括通过改变碳链长度，改变氢键的数目并替换异头原子来改变疏水性。化学合成通过使用各种方法进行并详细讨论。在人神经母细胞瘤细胞系SH-SY5Y中证实了这些类似物的神经生成活性。发现神经节苷脂Hp-s1类似物比神经节苷脂Hp-s1具有更高的IL-17A转录上调活性。
• Glycolipid derivatives, process for production of the same, intermediates for synthesis thereof, and process for production of the intermediates
  申请人：Japan as represented by President of National Center of Neurology and Psychiatry Ministry of Health

  公开号：EP2343306A1

  公开（公告）日：2011-07-13

  Novel glycolipid derivatives, where the substituent of the sphingosine base part is a short carbon chain alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group or substituted or unsubstituted aralkyl group and efficient synthetic methods for practical mass production of the same and intermediates useful for the synthesis of these compounds. Glycolipids having the formula (I): where R3 indicates a substituted or unsubstituted C1 to C7 linear alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted aralkyl group and R8 indicates a substituted or unsubstituted C1 to C35 alkyl group, substituted or unsubstituted aryl group or substituted or unsubstituted aralkyl group are chemically synthesized.

  新型糖脂衍生物（其中鞘磷脂基部分的取代基为短碳链烷基、取代或未取代的环烷基、取代或未取代的芳基或取代或未取代的芳烷基）以及用于实际大规模生产这些衍生物的高效合成方法和用于合成这些化合物的中间体。 具有式 (I) 的糖脂： 其中 R3 表示取代或未取代的 C1 至 C7 直链烷基、取代或未取代的环烷基、取代或未取代的芳基或取代或未取代的芳烷基，R8 表示取代或未取代的 C1 至 C35 烷基、取代或未取代的芳基或取代或未取代的芳烷基。
• Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile
  作者：Tetsuya Toba、Kenji Murata、Junko Futamura、Kyoko Nakanishi、Bitoku Takahashi、Naohiro Takemoto、Minako Tomino、Takashi Nakatsuka、Seiichi Imajo、Megumi Goto、Takashi Yamamura、Sachiko Miyake、Hirokazu Annoura

  DOI：10.1016/j.bmc.2012.03.025

  日期：2012.5

  A series of truncated analogs of alpha-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-gamma ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. (C) 2012 Elsevier Ltd. All rights reserved.
• NEW GLYCOLIPIDS AND SYNTHETIC METHOD THEREOF AS WELL AS THEIR SYNTHETIC INTERMEDIATES, AND SYNTHETIC METHOD THEREOF
  申请人：ANNOURA Hirokazu

  公开号：US20100210828A1

  公开（公告）日：2010-08-19

  Novel glycolipid derivatives, where the substituent of the sphingosine base part is a short carbon chain alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group or substituted or unsubstituted aralkyl group and efficient synthetic methods for practical mass production of the same and intermediates useful for the synthesis of these compounds. Glycolipids having the formula (I): where R 3 indicates a substituted or unsubstituted C 1 to C 7 linear alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted aralkyl group and R 8 indicates a substituted or unsubstituted C 1 to C 35 alkyl group, substituted or unsubstituted aryl group or substituted or unsubstituted aralkyl group are chemically synthesized.
• US7732583B2
  申请人：——

  公开号：US7732583B2

  公开（公告）日：2010-06-08