(2R)-2r,3c,4t,6t-tetrahydroxy-5c-methoxy-cyclohexanone | 3559-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2r,3c,4t,6t-tetrahydroxy-5c-methoxy-cyclohexanone
• 英文别名: (2R)-2r,3c,4t,6t-Tetrahydroxy-5c-methoxy-cyclohexanon；5-O-Methyl-L-myo-inosose-(1); 5-O-Methyl-(+)vibo-inosose；5-O-Methyl-meso-inosose-(3)；2D-5-O-methyl-2,3,5/4,6-pentahydroxycyclohexanone；(2R,3R,4R,5S,6R)-2,3,4,6-tetrahydroxy-5-methoxycyclohexan-1-one
• CAS: 3559-01-1；5834-35-5；20095-97-0；92541-30-5；92541-35-0；92541-36-1
• 化学式: C₇H₁₂O₆
• 分子量: 192.169
• InChiKey: VKPFEZAOAAZDPP-QCNSFQOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-2r,3c,4t,6t-tetrahydroxy-5c-methoxy-cyclohexanone 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 生成 2-O-Methyl-(+)-cyclohexan-1,3/2,4-tetrol
  参考文献：
  名称：

  Cyclitols and their Methyl Ethers. III. Catalytic Air Oxidation, the Hydrogenolysis of Inososes, and Some Pentol and Tetrol Methyl Ethers^1-3

  摘要：

  DOI：

  10.1021/ja00862a030
• 作为产物：
  描述：

  D-松醇 在 platinum on activated charcoal 氧气 作用下， 以 水 为溶剂， 生成 (2R)-2r,3c,4t,6t-tetrahydroxy-5c-methoxy-cyclohexanone
  参考文献：
  名称：

  Cyclitols and their Methyl Ethers. III. Catalytic Air Oxidation, the Hydrogenolysis of Inososes, and Some Pentol and Tetrol Methyl Ethers^1-3

  摘要：

  DOI：

  10.1021/ja00862a030

文献信息

• Inositol Methyl Ethers. II. The Formula of Sequoyitol^1-3
  作者：Laurens Anderson、Emily S. DeLuca、Albert Bieder、Gerald G. Post

  DOI：10.1021/ja01562a037

  日期：1957.3
• Enzymic Epimerization of Sequoyitol to d-Pinitol in Trifolium incarnatum
  作者：H. Ruis、O. Hoffmann-Ostenhof

  DOI：10.1111/j.1432-1033.1969.tb19629.x

  日期：1969.1

  The partial purification of an enzyme system from Trifolium incarnatum catalyzing the epimerization of sequoyitol to d‐pinitol and its characterization is described. The reaction proceeds via a keto intermediate, d‐5‐O‐methyl‐2,3,5/4,6‐pentahydroxycyclohexanone, and is catalyzed by two dehydrogenases or one protein with two dehydrogenase actions, of which the first one is NAD‐specific and oxidizes sequoyitol to the keto intermediate, whereas the other has the function to reduce the keto compound to d‐pinitol using NADPH as hydrogen donor. Both dehydrogenase actions as well as the overall epimerization reaction were shown to be reversible.Although the sequoyitol dehydrogenase activity can be easily destroyed by several means which leave the d‐pinitol dehydrogenase activity intact, no real separation of the two activities has been achieved. The protein or proteins responsible for the two activities have a molecular weight of about 34,000 as determined by the gel filtration method.The two activities do not only differ in their sensitivity towards inhibitors, their substrate and coenzyme specificities, but also in their stereospecificity with respect to the coenzymes. Whereas the NAD‐specific sequoyitol dehydrogenase activity is B‐specific, the NADP‐specific d‐pinitol dehydrogenase activity shows A‐specificity. On the basis of these findings, a possible mechanism for the epimerization is discussed.
• <b>Cyclitols and their Methyl Ethers. III. Catalytic Air Oxidation, the Hydrogenolysis of Inososes, and Some Pentol and Tetrol Methyl Ethers^1-3</b>
  作者：Gerald G. Post、Laurens. Anderson

  DOI：10.1021/ja00862a030

  日期：1962.2