methyl β-D-arabino-hexopyranosid-2-ulose | 2460-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl β-D-arabino-hexopyranosid-2-ulose
• 英文别名: methyl β-D-arabino-2-hexopyranosidulose；methyl 2-keto-β-D-glucopyranoside；O¹-Methyl-β-D-arabino-[2]hexosul-1,5-ose；Methyl-β-D-arabino-hexopyranosid-2-ulose；Methyl-β-D-arabino-hexopyranosidulose；(2R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-one
• CAS: 2460-41-5
• 化学式: C₇H₁₂O₆
• 分子量: 192.169
• InChiKey: ISRHTFSJNHPZNP-YCHQMNKZSA-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-arabino-hexopyranosid-2-ulose 在 水 、 铂 作用下， 生成 Methyl mannoside
  参考文献：
  名称：

  Theander, Acta Chemica Scandinavica (1947), 1958, vol. 12, p. 1887,1895

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基 Β-D-吡喃葡萄糖苷 在 sodium hypochlorite 作用下， 生成 methyl β-D-arabino-hexopyranosid-2-ulose
  参考文献：
  名称：

  Theander, Svensk Papperstidning (1943), 1958, vol. 61, p. 581,584

  摘要：

  DOI：

文献信息

• Utilization of Sugars in Organic Synthesis; Part XXVII. Chemistry of Oxo-Sugars. (2). Regio- and Stereo-Selective Synthesis of Methyl D-Hexopyranosiduloses and Identification of Their Forms Existing in Solutions.
  作者：Hong-Min LIU、Yoshiyuki SATO、Yoshisuke TSUDA

  DOI：10.1248/cpb.41.491

  日期：——

  Sixteen oxo derivatives of methyl D-hexopyranosides with various regio- and stereo-chemistries were selectively synthesized by direct oxidation of non-protected methyl glycosides by the bistributyltin oxide-bromine method or by oxidation of pfrtially protected glycosides followed by deprotection. The forms of these oxoglycosides existing in pryidine-d5 and in H2O (D2O) were investigated by means of 13C-NMR spectroscopy, and it was found that interconversion between oxo and hydrate forms of oxoglycosides readily takes place.

  通过双二丁基氧化锡-溴法直接氧化未受保护的甲基糖苷，或先氧化受部分保护的糖苷再进行脱保护，选择性地合成了十六种具有不同区域和立体化学结构的甲基 D-吡喃己苷的氧化衍生物。通过 13C-NMR 光谱法研究了这些氧化糖苷在 Pryidine-d5 和 H2O（D2O）中的存在形式，发现氧化糖苷的氧化形式和水合物形式之间很容易发生相互转化。
• Utilization of Sugars in Organic Synthesis. Part XXVI. Chemistry of Oxo-Sugars (1). Rearrangement of 2-Oxoglycosides in Pyridine: Evidence of Intramolecular Hydride Shift.
  作者：Yoshisuke TSUDA、Hong-Min LIU

  DOI：10.1248/cpb.40.1975

  日期：——

  Methyl α- and β-D-arabinohexopyranosid-2-uloses rearranged, in pyridine, into methyl α- and β-D-ribo-hexopyranosid-3-uloses through intermediacy of methyl α- and β-D-arabinohexopyranosid-3-uloses, respectively, indicating that an intramolecular hydride shift is the initial reaction for rearrangement of 2-oxoglycosides.

  甲基 α- 和 β-D-arabinoxopyranosid-2-uloses 在吡啶中分别通过中间体甲基 α- 和 β-D-arabinoxopyranosid-3-uloses 重排为甲基 α- 和 β-D-ribo-hexopyranosid-3-uloses ，这表明分子内氢化物转移是 2-氧代糖苷重排的初始反应。
• PYRAZOLE DERIVATIVE, MEDICINAL COMPOSITION CONTAINING THE SAME, MEDICINAL USE THEREOF AND INTERMEDIATE IN PRODUCING THE SAME
  申请人：Fujikura Hideki

  公开号：US20100029919A1

  公开（公告）日：2010-02-04

  The present invention provides pyrazole derivatives represented by the general formula: wherein R 1 represents H, an optionally substituted C 1-6 alkyl group etc.; one of Q and T represents a group selected from the following groups: , and the other represents —(CH 2 ) n —Ar wherein Ar represents an optionally substituted C 6-10 aryl group or an optionally substituted C 1-9 heteroaryl group; and n represents an integral number from 0 to 2 , an optionally substituted C 1-6 alkoxyl group, an optionally substituted amino group, an optionally substituted C 2-9 heterocycloalkyl group or an optionally substituted heterocycle-fused phenyl group; R represents an optionally substituted C 3-8 cycloalkyl group, an optionally substituted C 6-10 aryl group etc., pharmaceutically acceptable salts thereof or prodrugs thereof, which exhibit an excellent inhibitory activity in human 1,5 -anhydroglucitol/fructose/mannose transporter and are useful as agents for the prevention, inhibition of progression or treatment of a disease associated with the excess uptake of at least a kind of carbohydrates selected from glucose, fructose and mannose or a disease associated with hyperglycemia (e.g., diabetic complications, diabetes, etc.), and pharmaceutical compositions comprising the same, pharmaceutical uses thereof, and intermediates for production thereof.

  本发明提供了由下式表示的吡唑衍生物： 其中R1表示氢、可选取代的C1-6烷基等；Q和T中的一个表示以下组之一：， 另一个表示—(CH2)n—Ar，其中Ar表示可选取代的C6-10芳基或可选取代的C1-9杂环芳基；n表示0到2的整数，可选取代的C1-6烷氧基、可选取代的氨基、可选取代的C2-9杂环烷基或可选取代的杂环融合苯基；R表示可选取代的C3-8环烷基、可选取代的C6-10芳基等，其药物可接受的盐或前药，其在人类1,5-脱水葡萄糖/果糖/甘露糖转运体中具有出色的抑制活性，并且可用作预防、阻止进展或治疗与葡萄糖、果糖和甘露糖中至少一种过量摄入或与高血糖症（例如糖尿病并发症、糖尿病等）相关的疾病的药物，以及包含它们的制药组合物、制药用途和其制备的中间体。
• 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.
• Theander, Acta Chemica Scandinavica (1947), 1957, vol. 11, p. 1557,1562
  作者：Theander

  DOI：——

  日期：——