2-azido-D-ribo-1,3,4-decanetriol | 745041-51-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-azido-D-ribo-1,3,4-decanetriol
• 英文别名: (2S,3S,4R)-2-azidodecane-1,3,4-triol
• CAS: 745041-51-4
• 化学式: C₁₀H₂₁N₃O₃
• 分子量: 231.295
• InChiKey: GQPAQJNVAUNFRE-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-azido-D-ribo-1,3,4-decanetriol 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 42.0h， 生成 Acetic acid (1S,2R)-2-acetoxy-1-((S)-2-acetoxy-1-acetylamino-ethyl)-octyl ester
  参考文献：
  名称：

  A new diorganozinc-based enantioselective access to truncated d-ribo-phytosphingosine

  摘要：

  The use of a trans alpha,beta-epoxyaldehyde as a precursor Of D-ribo-phytosphingosines was studied. The highly stereoselective alkylation of the aldehyde with a diorganozinc reagent was ensured through double asymmetric induction. The regioselective opening of the epoxide in turn gives access to an azide from which a C-10 phytosphingosine can be easily prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02526-1
• 作为产物：
  描述：

  (R)-1-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-oxiranyl]-heptan-1-ol 在 sodium azide 、 氯化铵 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 乙二醇甲醚 、 水 为溶剂， 反应 32.0h， 生成 2-azido-D-ribo-1,3,4-decanetriol
  参考文献：
  名称：

  A new diorganozinc-based enantioselective access to truncated d-ribo-phytosphingosine

  摘要：

  The use of a trans alpha,beta-epoxyaldehyde as a precursor Of D-ribo-phytosphingosines was studied. The highly stereoselective alkylation of the aldehyde with a diorganozinc reagent was ensured through double asymmetric induction. The regioselective opening of the epoxide in turn gives access to an azide from which a C-10 phytosphingosine can be easily prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02526-1

文献信息

• 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.
• US8034908B2
  申请人：——

  公开号：US8034908B2

  公开（公告）日：2011-10-11
• A new diorganozinc-based enantioselective access to truncated d-ribo-phytosphingosine
  作者：Tahar Ayad、Yves Génisson、Alexandre Verdu、Michel Baltas、Liliane Gorrichon

  DOI：10.1016/s0040-4039(02)02526-1

  日期：2003.1

  The use of a trans alpha,beta-epoxyaldehyde as a precursor Of D-ribo-phytosphingosines was studied. The highly stereoselective alkylation of the aldehyde with a diorganozinc reagent was ensured through double asymmetric induction. The regioselective opening of the epoxide in turn gives access to an azide from which a C-10 phytosphingosine can be easily prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.