(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol | 664355-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol
• 英文别名: 1,5-dideoxy-2-C-hydroxymethyl-1,5-imino-L-lyxitol；3,4,5-Piperidinetriol, 3-(hydroxymethyl)-, (3R,4R,5S)-
• CAS: 664355-16-2
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: OXCYMYPLNFRTNJ-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1R,6R)-1-(hydroxymethyl)-3-[(1S)-1-phenylethyl]-7-oxa-3-azabicyclo[4.1.0]heptan-2-one 在 盐酸 、 Oxone 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate dihydrate 、 乙二胺四乙酸 、 dimethyl sulfide borane 、 硫酸 、 20% palladium hydroxide-activated charcoal 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 50.0 ℃ 、689.49 kPa 条件下， 反应 147.25h， 生成 (3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol
  参考文献：
  名称：

  The use of sodium chlorite in the non-racemic synthesis of a potent inhibitor of glycolipid biosynthesis

  摘要：

  A facile and environmentally friendly synthesis of both enantiomers of a biologically important 1-N-iminosugar (azasugar) is presented. To this end, the use of a very cheap and non-toxic reagent, such as sodium chlorite, is featured in two key reactions. Additionally, a highly stereoselective epoxidation with dimethyloxirane (DMDO), and regioselective acid-catalyzed epoxide ring opening are also two environmentally friendly reactions that are employed in this synthesis. For all the above-mentioned, and also taking into account that protecting groups were not employed, we would like to present this synthetic route as an efficient approach for the development of environmental and sustainable syntheses of highly oxygenated biologically important compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.08.054

文献信息

• Synthesis and evaluation of the glycosidase inhibitory activity of 5-hydroxy substituted isofagomine analogues
  作者：Mohammed M. Matin、Tarun Sharma、Sushma G. Sabharwal、Dilip D. Dhavale

  DOI：10.1039/b418283a

  日期：——

  An efficient strategy for the synthesis of 5-hydroxy substituted isofagomine analogues and , having both -CH2OH/CH3 and -OH functionality at the C-5 position, and evaluation of their inhibitory potency is reported. The synthetic methodology involves the aldol-Cannizzaro reaction of easily available alpha-d-xylopentodialdose followed by hydrogenolysis to afford the triol . Selective amidation of the

  报道了一种合成5-羟基取代的异黄花碱类似物和的有效策略，并在C-5位置同时具有-CH2OH / CH3和-OH官能团，并对它们的抑制效能进行了评估。合成方法涉及容易获得的α-d-二甲苯基戊二醛糖的aldol-Cannizzaro反应，然后进行氢解得到三醇。对C-4处的α-和β-羟甲基进行选择性酰胺化，1,2-丙酮化物基团的脱保护和氢化反应得到目标分子，发现它们对β-糖苷酶有效，IC50值在微摩尔范围内。该化合物对糖苷酶和人唾液淀粉酶显示出优异的效力。
• Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2
  作者：Michela I. Simone、Raquel G. Soengas、Sarah F. Jenkinson、Emma L. Evinson、Robert J. Nash、George W.J. Fleet

  DOI：10.1016/j.tetasy.2012.03.007

  日期：2012.3

  Homochiral piperidines containing a quaternary carbon branch at C-2 of the piperidine ring may be made from readily available carbohydrate lactones containing a branched 2-C-hydroxymethyl substituent. This gives an easy access to the branched iininosugars. In particular a trihydroxypipecolic acid analogue, (3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid, has been synthesised efficiently from the starting material D-ribose and (35,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol was found to be a specific inhibitor of alpha-D-glucosidase from Bacillus Stearothermophilus with an IC50 value of 93 mu M. (C) 2012 Elsevier Ltd. All rights reserved.
• The use of sodium chlorite in the non-racemic synthesis of a potent inhibitor of glycolipid biosynthesis
  作者：Carlos G. Gómez-Fosado、Leticia Quintero、Lilia Fuentes、Fernando Sartillo-Piscil

  DOI：10.1016/j.tetlet.2015.08.054

  日期：2015.10

  A facile and environmentally friendly synthesis of both enantiomers of a biologically important 1-N-iminosugar (azasugar) is presented. To this end, the use of a very cheap and non-toxic reagent, such as sodium chlorite, is featured in two key reactions. Additionally, a highly stereoselective epoxidation with dimethyloxirane (DMDO), and regioselective acid-catalyzed epoxide ring opening are also two environmentally friendly reactions that are employed in this synthesis. For all the above-mentioned, and also taking into account that protecting groups were not employed, we would like to present this synthetic route as an efficient approach for the development of environmental and sustainable syntheses of highly oxygenated biologically important compounds. (C) 2015 Elsevier Ltd. All rights reserved.