(2S,3S,4R)-5-hexene-1,2,3,4-tetrol | 139404-79-8

• 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)-5-hexene-1,2,3,4-tetrol
• 英文别名: 5,6-dideoxy-D-xylo-hex-5-enitol；L-xylo-1,2-dideoxy-hex-1-enitol；D-xylo-Hex-5-en-1,2,3,4-tetraol；L-xylo-1,2-Didesoxy-hex-1-enit；5,6-Sorbitoleen；(2S,3S,4R)-hex-5-ene-1,2,3,4-tetrol
• CAS: 139404-79-8
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: OOJKXRODCPMZDZ-SRQIZXRXSA-N

物化性质

• 沸点：
  371.1±42.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-5-hexene-1,2,3,4-tetrol 在 臭氧 、 sodium sulfite 作用下， 生成 L-木糖
  参考文献：
  名称：

  Substrate specificity and carbohydrate synthesis using transketolase

  摘要：

  This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis. The properties of transketolase from both yeast and spinach were investigated. The yeast enzyme was found to be more convenient for routine use. Examination of the substrate specificity of yeast transketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates. A practical protocol for transketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.

  DOI：

  10.1021/jo00048a023
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 (2S,3S,4R)-5-hexene-1,2,3,4-tetrol
  参考文献：
  名称：

  112.二硫醇。第六部分 2：3-二巯基丙醇与甘露醇和山梨糖醇的醚

  摘要：

  DOI：

  10.1039/jr9500000591

文献信息

• Synthesis of 3,5-Anhydro-2-deoxy-1,4-glyconolactones by Palladium(II)-Catalyzed, Regioselective Oxycarbonylation of C₅- and C₆-Enitols. ω-Homologation of Aldoses to Produce Intermediates for<i>C</i>-Glycoside/<i>C</i>-Nucleoside Synthesis
  作者：Tibor Gracza、Thomas Hasenöhrl、Ulrich Stahl、Volker Jäger

  DOI：10.1055/s-1991-28400

  日期：——

  The palladium(II)-catalyzed oxycarbonylation, known with alkenols and alkenediols, is studied with optically active 4-pentenitols (-triols) 1, 7 and 5-hexenitols (-tetrols) 12, 15, 18. Efficient routes for the substrates are provided, mostly from carbohydrate precursors. In all cases, bicyclic 3,6-anhydro-2-deoxy-1, 4-glyconolactones, versatile intermediates of C-glycosidic structure, are isolated with high selectivity and in good yield (53-77%). Several minor products (4-14% of regio-/diastereoisomers) from two competing pathways are observed and identified. The oxycarbonylation of alkenitols thus completes a novel sequence that transforms aldoses into homologous anhydro-glyconolactones, by C1-elongation at the terminal site. In the key step, the 3,4-threo arrangement is produced, from each of the four diastereomeric alkenitols studied (of the 6 cases available in the C5 and C6 series). The stereochemical protocol is summarized, e.g., by the transition D-gluco (aldose) → D-xylo (hexenitol, 15) → L-ido (anhydro-deoxyheptenolactone 26), as demonstrated.

  使用钯(II)催化氧羰基化己烯醇和烯二醇已知的方法，研究了光学活性的4-戊烯氮醇（三醇）1、7和5-己烯氮醇（四醇）12、15、18。提供了一种高效的路径，大部分以碳水化合物为底物。在所有情况下,双环3,6-脱水-2-脱氧-1,4-甘露环酮,C-糖苷结构的多种中间体,均以高选择性和较好的产率被分离出来(53-77%)。观察和识别了来自两个竞争途径的数个次要产品(4-14%的位/对映异构体)。烯氮醇的氧羰基化完成了一个将醛糖转化为同源脱水甘露醇环酮的新序列,通过在末端位点的C1延伸。在关键步骤中，从所研究的四种差向异构的烯醇(C5和C6系列共有6个)中，每个都产生了3,4-苏型排列。例如，通过D-葡萄糖(醛糖) → D-木糖(己烯醇,15) → L-艾杜糖(脱氧庚烯环酮26)这样的过渡，来证明立体化学的规程。
• 112. Dithiols. Part VI. Ethers of 2 : 3-dimercaptopropanol with mannitol and sorbitol
  作者：Peter Bladon、L. N. Owen

  DOI：10.1039/jr9500000591

  日期：——
• Substrate specificity and carbohydrate synthesis using transketolase
  作者：Yoshihiro Kobori、David C. Myles、George M. Whitesides

  DOI：10.1021/jo00048a023

  日期：1992.10

  This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis. The properties of transketolase from both yeast and spinach were investigated. The yeast enzyme was found to be more convenient for routine use. Examination of the substrate specificity of yeast transketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates. A practical protocol for transketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.