2,4-di-O-acetyl-3-deoxy-L-glycero-tetronic acid | 153704-84-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,4-di-O-acetyl-3-deoxy-L-glycero-tetronic acid
• 英文别名: (S)-2,4-diacetoxybutanoic acid；(2S)-2,4-diacetyloxybutanoic acid
• CAS: 153704-84-8
• 化学式: C₈H₁₂O₆
• 分子量: 204.18
• InChiKey: YMOXEZARHXTQLJ-ZETCQYMHSA-N

物化性质

• 沸点：
  347.0±32.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-di-O-acetyl-3-deoxy-L-glycero-tetronic acid 、 (2R,3R,4S,5S,6S)-4-Benzyloxy-6-[2-([1,3]dioxolan-2-ylmethoxy)-ethoxy]-5-methoxy-2-methyl-tetrahydro-pyran-3-ylamine 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以82%的产率得到4-(1,3-dioxolan-2-yl)-3-oxabutyl 3-O-benzyl-2-O-methyl-4,6-dideoxy-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of theVibrio CholeraeO1 Ogawa and Inaba Terminal Disaccharides With Dioxolane-Type Spacers and their Coupling to Proteins¹

  摘要：

  The disaccharide, which corresponds to the terminal fragment of the Vibrio cholerae O1 LPS, was prepared starting from the corresponding trichloroacetimidate derivative of the monosaccharide in the presence of trimethylsilyl triflate. After selective reduction of the azido group, the reaction with 2,4-di-O-acetyl-3-deoxy-L-glycero-tetronic acid in the presence of EEDQ afforded the corresponding amides. The cleavage of dioxolane protecting group followed by careful deacetylation and coupling with Bovine Serum Albumin or Meningococcal Outer Membrane Protein in the presence of sodium cyanoborohydride gave the corresponding neoglycoconjugates.

  DOI：

  10.1080/07328309808002355
• 作为产物：
  描述：

  (S)-1-phenylpropane-1,3-diyl diacetate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 22.0h， 生成 2,4-di-O-acetyl-3-deoxy-L-glycero-tetronic acid
  参考文献：
  名称：

  Efficient synthesis of mugineic acid, a typical phytosiderophore, utilizing the phenyl group as the carboxyl synthon

  摘要：

  Stereoselective total synthesis of mugineic acid, a unique phytosiderophore from roots of barley, has been achieved from (2R,3R)- and (2S,3S)-2,3-epoxycinnamyl alcohols employing the phenyl group as the carboxyl synthon.

  DOI：

  10.1016/s0040-4039(00)74778-2

文献信息

• Towards the complete synthetic O-antigen of <i>Vibrio cholerae</i> O1, serotype inaba: improved synthesis of the conjugation-ready upstream terminal hexasaccharide determinant
  作者：Mana Mohan Mukherjee、Peng Xu、Edwin D. Stevens、Pavol Kováč

  DOI：10.1039/c9ra08232h

  日期：——

  limited to optimized conditions for the stereoselectivity of glycosylation reactions involved and fewer number of synthetic steps, compared to previous approaches. Particularly noteworthy is conducting the glycosylation of the very reactive glycosyl acceptor 8-azido-3,6-dioxaoctanol with the fully assembled hexasaccharide trichloroacetimidate under thermodynamic control. It produced the desired α glycoside

  霍乱弧菌O1（血清型 Inaba）脂多糖（LPS）上游末端六糖部分的合成已得到改进。与以前的方法相比，关键的改进包括但不限于所涉及的糖基化反应的立体选择性的优化条件以及更少的合成步骤。特别值得注意的是，在热力学控制下，用完全组装的六糖三氯乙酰亚胺酯进行反应性极高的糖基受体8-叠氮基-3,6-二氧辛醇的糖基化。它产生了所需的 α ​​糖苷，其 α: β 比例为 7:1，而传统进行偶联时观察到的比例为 1.1:1。以前以合成中间体可接受的纯度获得的几种物质现在以分析纯状态获得并得到充分表征。通过单晶X射线结构测定证实了关键三糖糖基受体的结构。
• Total synthesis of mugineic acid. Efficient use of the phenyl group as the carboxyl synthon
  作者：Fumiyoshi Matsuura、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4020(01)88039-x

  日期：1993.9

  Stereoselective total synthesis of mugineic acid (1), a unique phytosiderophore from roots of barley, has been achieved from madily available (2S,3S)- and (2R,3R)-2,3-epoxycinnamyl alcohols (5) and (6). The key step is the oxidation of the phenyl group to the carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.