1,5-anhydro-2,3,4,6-tetra-O-methyl-D-mannitol | 6001-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2,3,4,6-tetra-O-methyl-D-mannitol
• 英文别名: 1,5-Anhydro-O²,O³,O⁴,O⁶-Tetramethyl-D-mannit；1,5-Anhydro-2,3,4,6-tetra-O-methyl-D-galactitol；(2R,3R,4R,5R)-3,4,5-trimethoxy-2-(methoxymethyl)oxane
• CAS: 6001-00-9
• 化学式: C₁₀H₂₀O₅
• 分子量: 220.266
• InChiKey: SQOPNOVHKFZFPJ-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tetra-O-acetyl-1,5-anhydro-D-mannitol 在 甲醇 、 四氯化碳 、 sodium hydroxide 、 sodium methylate 作用下， 生成 1,5-anhydro-2,3,4,6-tetra-O-methyl-D-mannitol
  参考文献：
  名称：

  The Structure of Styracitol¹

  摘要：

  DOI：

  10.1021/ja01231a047

文献信息

• Free‐Radical Epimerization of <scp>d</scp> ‐ into <scp>l</scp> ‐ <i>C</i> ‐(Glycosyl)methanol Compounds Using 1,5‐Hydrogen Atom Transfer Reaction
  作者：Adrián S. Montes、Elisa I. León、Ángeles Martín、Inés Pérez‐Martín、Ernesto Suárez

  DOI：10.1002/ejoc.202101391

  日期：2022.4.27

  C5 of readily accessible d- or l-carbohydrates, by means of a remote reductive radical sequence was described. A comparative study of the radical process promoted by a tin reagent or with photoredox conditions was also performed. The stereochemical and polarity influence of the substituents in the course of the radical sequence was considered.

  描述了通过远程还原自由基序列在容易获得的d-或l-碳水化合物的 C5 处进行长程差向异构化制备对映异构纯的顺式- C - 糖基化合物。还进行了由锡试剂或光氧化还原条件促进的自由基过程的比较研究。考虑了取代基在自由基序列过程中的立体化学和极性影响。
• Determination of polysaccharide linkage and branching by reductive depolymerization. Gas-liquid chromatography and gas-liquid chromatography-mass spectrometry reference data
  作者：Agnes Van Langenhove、Vernon N. Reinhold

  DOI：10.1016/s0008-6215(00)90691-8

  日期：1985.11

  A series of partially methylated anhydro-D-alditol acetates has been prepared and analyzed by g.l.c. and g.l.c.-m.s. The reference compounds were obtained by reductive cleavage of permethylated and partially methylated standard methyl glycosides, and standard di-, tri-, and tetra-saccharides of known composition and linkage. Structural characterization included retention times on g.l.c. using DB-225

  制备了一系列部分甲基化的无水D-醛糖醇乙酸酯，并通过glc和glc-ms分析。参比化合物是通过还原裂解全甲基化和部分甲基化的标准甲基糖苷以及标准的二，三和四已知组成和连接的糖。结构表征包括使用DB-225毛细管色谱柱在glc上的保留时间以及在化学和电离模式下的质谱分析。这个编译的库允许进一步评估还原性切割程序用于确定新的和更复杂的寡糖的连接或分支（或两者）的适用性。该技术已应用于微克量的细菌膜寡糖和从甘露糖苷病患者的尿液中获得的糖类。
• Mechanism of the reductive cleavage reaction of permethylated methyl d-glycopyranosides
  作者：Chang Kiu Lee、Eun Ju Kim

  DOI：10.1016/s0008-6215(99)00157-3

  日期：1999.8

  Abstract The mechanism of the reductive cleavage reaction of permethylated methyl d -glycopyranosides was investigated by measuring the rate of reaction. Glycosides employed were of α-Glc, β-Glc, α-Man, α-Gal, and β-Gal. Seven silanes were used to explore the reactivities of the reducing agents as well as to examine the stereoelectronic effects of the agents. Trimethylsilyl trifluoromethanesulfonate

  摘要通过测量反应速率，研究了全甲基化甲基d-吡喃葡萄糖苷的还原裂解反应机理。使用的糖苷是α-Glc，β-Glc，α-Man，α-Gal和β-Gal。七种硅烷用于探索还原剂的反应性以及检查还原剂的立体电子效应。三氟甲磺酸三甲基甲硅烷基酯用作催化剂。通常，β-端基异构体的速率大约是α-端基异构体的速率的两倍。异构化速率比还原速率低约五到十倍。有人提议将环状氧鎓离子作为还原性裂解α-糖苷键的唯一中间体，
• The Chemistry of Naturally Occurring Monoanhydrohexitols. II. Synthetic Tetramethylstyracitol¹
  作者：Werner Freudenberg、John T. Sheehan

  DOI：10.1021/ja01860a032

  日期：1940.3
• Reductive cleavage of glycosides
  作者：David Rolf、Gary R. Gray

  DOI：10.1021/ja00376a065

  日期：1982.6