1-propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 722544-09-4

• 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
• 英文名称: 1-propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: n-propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside；propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• CAS: 722544-09-4
• 化学式: C₁₇H₂₆O₁₀
• 分子量: 390.387
• InChiKey: CWUMLQVHOLFZBX-NRKLIOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 3.0h， 以123 mg的产率得到1-propyl α-D-mannopyranoside
  参考文献：
  名称：

  Discovery of the Chemical Function of Glycosidases:  Design, Synthesis, and Evaluation of Mass-Differentiated Carbohydrate Libraries

  摘要：

  Discovery of the catalytic chemical function of the many putative glycosidases coded in genomes currently relies on individual testing of possible substrates, usually as their p-nitrophenol conjugate. Herein, we present an alternative chemical proteomics approach using a synthetic mass-differentiated heat-stable substrate library with mass spectrometry readout. Library components do not serve as reaction inhibitors and both primary and secondary enzyme substrates can be delineated.

  DOI：

  10.1021/ol049389b
• 作为产物：
  描述：

  D-甘露糖 在 吡啶 、 Dowex-50W X-8H⁺-400 作用下， 反应 18.0h， 生成 1-propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Discovery of the Chemical Function of Glycosidases:  Design, Synthesis, and Evaluation of Mass-Differentiated Carbohydrate Libraries

  摘要：

  Discovery of the catalytic chemical function of the many putative glycosidases coded in genomes currently relies on individual testing of possible substrates, usually as their p-nitrophenol conjugate. Herein, we present an alternative chemical proteomics approach using a synthetic mass-differentiated heat-stable substrate library with mass spectrometry readout. Library components do not serve as reaction inhibitors and both primary and secondary enzyme substrates can be delineated.

  DOI：

  10.1021/ol049389b

文献信息

• C-C Bond Formation by Sequential Intramolecular Hydrogen Atom Transfer/Intermolecular Radical Allylation Reaction in Carbohydrate Systems
  作者：Elisa I. León、Ángeles Martín、Inés Pérez-Martín、Luís M. Quintanal、Ernesto Suárez

  DOI：10.1002/ejoc.201200300

  日期：2012.7

  This work was supported by the Research Programs of the Gobierno de Canarias (SolSubC200801000192 and CTQ2010‐18244) of the Ministerio de Ciencia e Innovacion, cofinanced by the Fondo Europeo de Desarrollo Regional (FEDER). I. P.‐M. thanks the Spanish Ministerio de Ciencia e Innovacion for the Research Program PIE 200930I138. L. M. Q. thanks the Consejo Superior de Investigaciones Cientificas (CSIC)

  这项工作得到了德国科学与创新部长的 Gobierno de Canarias 研究计划 (SolSubC200801000192 和 CTQ2010-18244) 的支持，并由 Fondo Europeo de Desarrollo 地区 (FEDER) 共同资助。IP-M。感谢西班牙部长级 Ciencia e Innovacion 的研究计划 PIE 200930I138。LMQ 感谢 Consejo Superior de Investigaciones Cientificas (CSIC)（I3P 计划）提供的奖学金。
• Hydrogen Atom Transfer Experiments Provide Chemical Evidence for the Conformational Differences between C- and O-Disaccharides
  作者：Elisa I. León、Angeles Martín、Inés Peréz-Martín、Luis M. Quintanal、Ernesto Suárez

  DOI：10.1002/ejoc.201000470

  日期：2010.9

  promoted by alkoxyl radicals generated from 3-hydroxypropyl α- d -mannopyranoside derivative ( O -glycoside) and 2,6-anhydro- d - glycero - d - manno -decitol derivative ( C -glycoside) is studied. The O -glycoside model abstracts preferentially the hydrogen atom at C-5 (1,8-HAT) while the C -glycoside abstracts the hydrogen atom at C-1 (1,6-HAT) but no abstraction at C-5 could be detected. These results

  摘要 3-羟丙基α-d-吡喃甘露糖苷衍生物（O-糖苷）和2,6-脱水-d-甘油-d-甘露糖-癸醇衍生物（O-糖苷）产生的烷氧基促进了氢原子转移（HAT）反应的区域选择性（ C-糖苷）进行了研究。O-糖苷模型优先提取 C-5 (1,8-HAT) 处的氢原子，而 C-糖苷模型提取 C-1 (1,6-HAT) 处的氢原子，但不能提取 C-5 处的氢原子检测到。这些结果可以通过 O-糖苷中的外异头效应产生的立体电子控制来解释。
• Hydrogen atom transfer experiments provide chemical evidence for the conformational differences between C- and O-glycosides
  作者：Angeles Martín、Luis M. Quintanal、Ernesto Suárez

  DOI：10.1016/j.tetlet.2007.05.166

  日期：2007.7

  reaction promoted by alkoxyl radicals generated from 3-hydroxypropyl α-d-mannopyranoside derivative (O-glycoside) and 2,6-anhydro-d-glycero-d-manno-decitol derivative (C-glycoside) is studied. The O-glycoside model abstracts preferentially the hydrogen atom at C-5 (1,8-HAT) while the C-glycoside abstracts the hydrogen atom at C-1 (1,6-HAT) but no abstraction at C-5 could be detected. These results are explained

  3-羟丙基α-d-甘露吡喃糖苷衍生物（O-糖苷）和2,6-脱水-d-甘油-d-甘露糖醇衍生物（C -糖苷）。该Ô糖苷模型抽象优先在C-5（1,8-HAT）上的氢原子而Ç糖苷抽象在C-1（1,6-HAT）上的氢原子，但在C-5可以是没有抽象检测到。这些结果通过在O-糖苷中的外-异头作用所施加的立体电子控制来解释。