D-glycero-D-ido-oct-2-ulose | 1016606-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-glycero-D-ido-oct-2-ulose
• 英文别名: d-Glycero-d-ido-octulose；(3S,4R,5S,6R,7R)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one
• CAS: 1016606-96-4
• 化学式: C₈H₁₆O₈
• 分子量: 240.21
• InChiKey: KSHYQYHHIKNYAY-KYEGTCRESA-N

物化性质

• 沸点：
  686.1±55.0 °C(Predicted)
• 密度：
  1.690±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  159
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 乙氧基胺盐酸盐 、 D-glycero-D-ido-oct-2-ulose 生成
  参考文献：
  名称：

  Mass spectrometric studies of the path of carbon in photosynthesis: Positional isotopic analysis of13C-labelled 2-octulose phosphates

  摘要：

  AbstractThe electron impact mass spectrometric fragmentation patterns of the per‐O‐trimethylsilyl (TMS) and alkoxime‐TMS derivatives of D‐glycerol‐D‐altro and D‐glycerol‐D‐ido‐octuloses were fully analysed using seven specifically labelled 13C analogues. Many of the more intense‐ ions in the spectra of the per‐O‐TMS furanose and pyranose derivatives have more than one origin. On the other hand, the mass spectra of the straight‐chain methoxime and ethoxime hepta‐O‐TMS derivatives contain ions each of which in general originares from a single cleavage process. This makes gas chromatography/mass spectrometry of the aikoxime‐TMS derivatives a suitable method for monitoring 13C incorporations at individual carbon atoms in the corresponding octulose phosphates during photosynthesis experiments with 13CO2.

  DOI：

  10.1002/oms.1210271015
• 作为产物：
  描述：

  D-Glycero-D-ido-octulose 8-phosphate 生成 D-glycero-D-ido-oct-2-ulose
  参考文献：
  名称：

  Mass spectrometric studies of the path of carbon in photosynthesis: Positional isotopic analysis of13C-labelled 2-octulose phosphates

  摘要：

  AbstractThe electron impact mass spectrometric fragmentation patterns of the per‐O‐trimethylsilyl (TMS) and alkoxime‐TMS derivatives of D‐glycerol‐D‐altro and D‐glycerol‐D‐ido‐octuloses were fully analysed using seven specifically labelled 13C analogues. Many of the more intense‐ ions in the spectra of the per‐O‐TMS furanose and pyranose derivatives have more than one origin. On the other hand, the mass spectra of the straight‐chain methoxime and ethoxime hepta‐O‐TMS derivatives contain ions each of which in general originares from a single cleavage process. This makes gas chromatography/mass spectrometry of the aikoxime‐TMS derivatives a suitable method for monitoring 13C incorporations at individual carbon atoms in the corresponding octulose phosphates during photosynthesis experiments with 13CO2.

  DOI：

  10.1002/oms.1210271015

文献信息

• Stereospecific Synthesis of D-Glycero- D-ido-oct-2-ulose
  作者：Zuzana Hricovíniová、Miloš Hricovíni、Ladislav Petruš

  DOI：10.1007/s007060170088

  日期：2001.6

  3:6,7-di-O-isopropylidene derivative. Its base-catalyzed addition to formaldehyde resulted in the formation of 2,3:6,7-di-O-isopropylidene-2-C-(hydroxymethyl)- D -glycero- D -gulo-heptofuranose. After acid hydrolysis of this aldolization product, a new branched-chain aldose, 2-C-(hydroxymethyl)- D -glycero- D -gulo-heptose, was obtained, which was stereospecifically rearranged under the catalytic action

    D- 甘油 -D- 古洛庚糖与2，2-二甲氧基丙烷反应，得到其2，3：6，7-二-O-异亚丙基衍生物。其碱催化的向甲醛的加成导致形成2,3：6,7-二-O-异亚丙基-2-C-（羟甲基） -D- 甘油 -D -gulo-七呋喃糖。将该醛缩醛化产物酸水解后，获得了新的支链醛糖2-C-（羟甲基） -D- 甘油 -D -gu-庚糖，其在钼酸催化作用下立体定向重排为 D- 。甘油- d -ido-辛-2-酮糖。
• Isomerization as a route to rare ketoses: the beneficial effect of microwave irradiation on Mo(VI)-catalyzed stereospecific rearrangement
  作者：Zuzana Hricovíniová

  DOI：10.1016/j.tetasy.2007.11.025

  日期：2008.2

  aldoses to rare ketoses was achieved in 3 min using microwave flash heating. This contribution highlights the remarkable advantages of Mo(VI) catalysis and the beneficial effects of microwave irradiation in carbohydrate synthesis. The transformation yielded the respective ketoses in good yields (46–86%). Furthermore, the potential of the Mo(VI)-catalyzed transformation was studied using a new branched 6-deoxy-aldose

  使用微波快速加热，在3分钟内即可完成Mo（VI）催化的2- C-（羟甲基）支链醛糖的易于获得的异构化反应，转化为稀有的酮糖。这项贡献突出了Mo（VI）催化的显着优势以及微波辐射在碳水化合物合成中的有益作用。转化产生的各个酮糖产率很高（46-86％）。此外，使用新的支链6-脱氧醛糖来制备7-脱氧-1-葡萄糖-庚糖，研究了Mo（VI）催化转化的潜力。该方法快速有效，可用于在微波条件下制备稀有酮糖。
• Utilization of enzymes in organic chemistry: Transketolase catalyzed synthesis of ketoses
  作者：Jean Bolte、Colette Demuynck、Hamid Samaki

  DOI：10.1016/s0040-4039(00)96770-4

  日期：1987.1
• Hobbs, Gordon R.; Lilly, Malcolm D.; Turner, Nicholas J., Journal of the Chemical Society. Perkin transactions I, 1993, # 2, p. 165 - 166
  作者：Hobbs, Gordon R.、Lilly, Malcolm D.、Turner, Nicholas J.、Ward, John M.、Willets, Andrew J.、Woodley, John M.

  DOI：——

  日期：——
• Mass spectrometric studies of the path of carbon in photosynthesis: Positional isotopic analysis of13C-labelled 2-octulose phosphates
  作者：Robert W. Irvine、Ian L. Flanigan、John K. MacLeod、J. Grant Collins、John F. Williams

  DOI：10.1002/oms.1210271015

  日期：1992.10

  AbstractThe electron impact mass spectrometric fragmentation patterns of the per‐O‐trimethylsilyl (TMS) and alkoxime‐TMS derivatives of D‐glycerol‐D‐altro and D‐glycerol‐D‐ido‐octuloses were fully analysed using seven specifically labelled 13C analogues. Many of the more intense‐ ions in the spectra of the per‐O‐TMS furanose and pyranose derivatives have more than one origin. On the other hand, the mass spectra of the straight‐chain methoxime and ethoxime hepta‐O‐TMS derivatives contain ions each of which in general originares from a single cleavage process. This makes gas chromatography/mass spectrometry of the aikoxime‐TMS derivatives a suitable method for monitoring 13C incorporations at individual carbon atoms in the corresponding octulose phosphates during photosynthesis experiments with 13CO2.