1,2,3,6-四-O-苯甲酰基-alpha-D-甘露糖 | 56994-11-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1,2,3,6-四-O-苯甲酰基-alpha-D-甘露糖
• 中文别名: 2,5-二脱氧-2,5-亚氨基-D-葡萄糖醇
• 英文名称: 1,2,3,6-Tetra-O-benzoyl-α-D-mannopyranose
• 英文别名: 1,2,3,6-Tetra-O-benzoyl-a-D-mannopyranose；[(2R,3R,4S,5S,6R)-4,5,6-tribenzoyloxy-3-hydroxyoxan-2-yl]methyl benzoate
• CAS: 56994-11-7
• 化学式: C₃₄H₂₈O₁₀
• 分子量: 596.59
• InChiKey: IBHLAWIOLBRAAK-LSPAEZJRSA-N

物化性质

• 熔点：
  182-183°C
• 沸点：
  734.9±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,3,6-四-O-苯甲酰基-alpha-D-甘露糖 在 哌啶 、 吡啶 、 咪唑 、 三甲基乙酰氯 、 三乙胺 、 三氯化磷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 31.58h， 生成 1,2,3,6-Tetra-O-benzoyl-α-D-mannopyranose 4-phosphate bis(triethylammonium) salt
  参考文献：
  名称：

  Hydrogenphosphonate synthesis of sugar phosphomonoesters

  摘要：

  已经开发了一种高效的糖羟基衍生物磷酸化程序。该程序包括四个步骤：H-磷酸酯的形成、与弗罗伦-9-甲醇的pivaloyl氯介导的耦合、氧化以及弗罗伦-9-甲基酯的裂解，最终获得糖单磷酸衍生物4a-g，产率为83-93%。

  DOI：

  10.1039/b000727g
• 作为产物：
  描述：

  甘露糖 、 苯甲酰氯 以 吡啶 为溶剂， 以27%的产率得到1,2,3,6-四-O-苯甲酰基-alpha-D-甘露糖
  参考文献：
  名称：

  Nikolaev, Andrey V.; Rutherford, Trevor J.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1995, # 16, p. 1977 - 1988

  摘要：

  DOI：

文献信息

• An efficient and stereoselective synthesis of β-d-Arap-(1→2)-β-d-Galp-(1→3)-β-d-Galp-(1→4)-α-d-Manp, a tetrasaccharide fragment of Leishmania major lipophosphoglycan
  作者：Dmitry V Yashunsky、Adrian P Higson、Andrew J Ross、Andrei V Nikolaev

  DOI：10.1016/s0008-6215(01)00274-9

  日期：2001.12

  A tetrasaccharide fragment of Leishmania major lipophosphoglycan (which seems to be involved in a biological mechanism for the parasite transmission) has been synthesised using the thioglycoside, trichloroacetimidate and halide-exchange glycosylation procedures and step-wise chain elongation strategy.

  利什曼原虫主要脂质磷酸聚糖的四糖片段（似乎与寄生虫传播的生物学机制有关）已使用硫代糖苷，三氯乙酰亚胺酸酯和卤化物交换糖基化程序和逐步链延长策略合成。
• Parasite glycoconjugates. Part 5. Blockwise approach to oligo(glycosyl phosphates): chemical synthesis of a terminal tris(glycobiosyl phosphate) fragment of Leishmania donovani antigenic lipophosphoglycan
  作者：Andrei V. Nikolaev、Trevor J. Rutherford、Michael A. J. Ferguson、John S. Brimacombe

  DOI：10.1039/p19960001559

  日期：——

  The model tetramannosyl triphosphate 7 and the hexaglycosyl triphosphate 8, which is a terminal fragment of the phosphoglycan portion of Leishmania donovani lipophosphoglycan, have been synthesized. Elongation of the chain was performed using the glycosyl hydrogenphosphonate method to couple together two phosphodiester blocks.

  已经合成了模型四甘露糖基三磷酸 7 和六糖基三磷酸 8（杜氏利什曼原虫脂磷酸聚糖的磷酸聚糖部分的末端片段）。使用糖基膦酸氢法将两个磷酸二酯嵌段偶联在一起进行链的延长。
• The preparation of deoxy derivatives of mannose-1-phosphate and their substrate specificity towards recombinant GDP-mannose pyrophosphorylase from Salmonella enterica, group B
  作者：Gregory M Watt、Sabine L Flitsch、Sven Fey、Lothar Elling、Udo Kragl

  DOI：10.1016/s0957-4166(99)00556-x

  日期：2000.2

  2-Deoxy-alpha-D-glucose-1-phosphate, 3-deoxy-alpha-D-arabino-hexose-1-phosphate, 4-deoxy-alpha-D-lyxo-hexose-1-phosphate, and alpha-D-lyxose-1-phosphate were synthesised chemically, and evaluated as substrates for a recombinant GDP-mannose pyrophosphorylase (Salmonella enterica, group B, cloned in Escherichia coli). The deoxy derivatives were all substrates for the enzyme, with slightly reduced V-max values but significantly higher K-m values than those recorded for the native substrate, mannose-1-phosphate. The pyrophosphorylase was used for the synthesis of GDP-mannose analogues GDP-2-deoxy-glucose and GDP-lyxose on a milligram scale. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Ivanova, Irina A.; Ross, Andrew J.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1999, # 12, p. 1743 - 1753
  作者：Ivanova, Irina A.、Ross, Andrew J.、Ferguson, Michael A. J.、Nikolaev, Andrei V.

  DOI：——

  日期：——
• Higson, Adrian P.; Tsvetkov, Yury E.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1998, # 16, p. 2587 - 2595
  作者：Higson, Adrian P.、Tsvetkov, Yury E.、Ferguson, Michael A. J.、Nikolaev, Andrei V.

  DOI：——

  日期：——