methyl β-D-xylo-hexopyranoside-4-ulose | 32361-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl β-D-xylo-hexopyranoside-4-ulose
• 英文别名: methyl 4-keto-β-D-glucopyranoside；Methyl-β-D-xylo-hexopyranosid-4-ulose；Methyl I(2)-D-xylo-hexopyranosid-4-ulose；(2R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-one
• CAS: 32361-32-3
• 化学式: C₇H₁₂O₆
• 分子量: 192.169
• InChiKey: PXYUEYYQRRNNRU-VYNVVFCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl β-D-xylo-hexopyranoside-4-ulose 在 硫酸 作用下， 反应 3.0h， 以15 mg的产率得到3-羟基-2-(羟基甲基)-4H-吡喃-4-酮
  参考文献：
  名称：

  14C-tracer studies on the conversion of methyl β-d-ribo-hexosid-3-ulose into reductic acid (2,3-dihydroxycyclopenten-1-one)

  摘要：

  DOI：

  10.1016/s0008-6215(00)83842-2
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 phenyltrimethylammonium tribromide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以94%的产率得到methyl β-D-xylo-hexopyranoside-4-ulose
  参考文献：
  名称：

  Catalytic and Regioselective Oxidation of Carbohydrates To Synthesize Keto-Sugars under Mild Conditions

  摘要：

  A new catalytic and regioselective approach for the synthesis of keto-sugars is described. An organotin catalyst, Oc2SnCl2, in the presence of trimethylphenylammonium tribromide ([TMPhA](+)Br3(-)) accelerates the regioselective oxidation at the "axial"-OH group of 1,2-diol moieties in galactopyranosides. The reaction conditions can also be used for the regioselective oxidation of various carbohydrates.

  DOI：

  10.1021/ol502344h

文献信息

• Regioselective mono-oxidation of non-protected glycosides by the bis-tributyltin oxide-bromine method.
  作者：Yoshisuke Tsuda、Naohisa Matsuhira、Kimihiro (Yoshimoto) Kanemitsu

  DOI：10.1248/cpb.33.4095

  日期：——

  Treatment of methyl glycosides with an excess of bis-tributyltin oxide and molecular sieves 3A in chloroform followed by brominolysis resulted in monooxidation to yield oxo-glycosides regioselectively. Thus Me β-D-Glc and Me β-D-Xyl gave the 3-oxo derivatives in more than 90% yield, and Me α-D-Glc, Me α-D-Gal, Me α-D-Xyl, and Me β-L-Ara gave the 4-oxo derivatives in 70-80% yield.

  甲基糖苷与过量的二三丁基锡氧化物和分子筛3A在氯仿中反应，随后进行溴解反应，可以区域选择性地单氧化生成氧代糖苷。因此，Me β-D-葡糖苷和Me β-D-木糖苷以超过90%的产率得到3-氧代衍生物，而Me α-D-葡糖苷、Me α-D-半乳糖苷、Me α-D-木糖苷和Me β-L-阿拉伯糖苷以70-80%的产率得到4-氧代衍生物。
• Tsuda, Yoshisuke; Hanajima, Makiko; Matsuhira, Naohisa, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 9, p. 2344 - 2350
  作者：Tsuda, Yoshisuke、Hanajima, Makiko、Matsuhira, Naohisa、Okuno, Yukihiro、Kanemitsu, Kimihiro

  DOI：——

  日期：——
• TSUDA, YOSHISUKE;HANAJIMA, MAKIKO;MATSUHIRA, NAOHISA;OKUNO, YUKIHIRO;KANE+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2344-2350
  作者：TSUDA, YOSHISUKE、HANAJIMA, MAKIKO、MATSUHIRA, NAOHISA、OKUNO, YUKIHIRO、KANE+

  DOI：——

  日期：——
• Catalytic and Regioselective Oxidation of Carbohydrates To Synthesize Keto-Sugars under Mild Conditions
  作者：Wataru Muramatsu

  DOI：10.1021/ol502344h

  日期：2014.9.19

  A new catalytic and regioselective approach for the synthesis of keto-sugars is described. An organotin catalyst, Oc2SnCl2, in the presence of trimethylphenylammonium tribromide ([TMPhA](+)Br3(-)) accelerates the regioselective oxidation at the "axial"-OH group of 1,2-diol moieties in galactopyranosides. The reaction conditions can also be used for the regioselective oxidation of various carbohydrates.
• 14C-tracer studies on the conversion of methyl β-d-ribo-hexosid-3-ulose into reductic acid (2,3-dihydroxycyclopenten-1-one)
  作者：George L. Lookhart、Milton S. Feather、Goran Lindgren、Thomas Popoff、Olof Theander

  DOI：10.1016/s0008-6215(00)83842-2

  日期：1980.3