methyl-α-D-lyxofuranoside | 22416-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-α-D-lyxofuranoside
• 英文别名: methyl α-D-arabinofuranoside；Methyl α-D-lyxofuranoside；Methyl-α-D-lyxofuranosid；alpha-d-Lyxofuranoside, methyl；(2R,3R,4S,5S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol
• CAS: 22416-73-5
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: NALRCAPFICWVAQ-VANKVMQKSA-N

物化性质

• 熔点：
  93-94 °C
• 沸点：
  348.7±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.93
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl-α-D-lyxofuranoside 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.0h， 生成 methyl 2-O-benzyl-3,5-O-isopropylidene-α-D-lyxofuranoside
  参考文献：
  名称：

  Synthesis of fragments of a streptococcus pneumoniae type-specific capsular polysaccharide

  摘要：

  DOI：

  10.1016/s0040-4020(01)89206-1
• 作为产物：
  描述：

  D-lyxose 在 吡啶 、 二甲基乙基硼酸酯 作用下， 生成 methyl-α-D-lyxofuranoside
  参考文献：
  名称：

  Dahlhoff, Wilhelm V.; Fenzl, Wolfgang; Koester, Roland, Liebigs Annalen der Chemie, 1990, # 8, p. 807 - 810

  摘要：

  DOI：

文献信息

• GLYCOSIDATION OF SUGARS: II. METHANOLYSIS OF D-XYLOSE, D-ARABINOSE, D-LYXOSE, AND D-RIBOSE
  作者：C. T. Bishop、F. P. Cooper

  DOI：10.1139/v63-405

  日期：1963.11.1

  Rates of methanolysis reactions of D-xylose, D-arabinose, D-lyxose, and D-ribose have been determined. It was found that methanolysis of a pentose proceeds to equilibrium through four distinguishable, competing reactions: (1) pentose → furanosides; (2) anomerization of furanosides; (3) furanosides → pyranosides; (4) anomerization of pyranosides. The glycoside compositions at equilibrium are interpreted in terms of stabilities of each of the four glycosides from each sugar as influenced by steric and ionic effects; a system of conformational analysis of furanoside rings is presented. The free energies of reaction in anomerization of pyranosides were in excellent agreement with values calculated from previously reported interaction energies in the pyranoid ring. The relative rates of the reactions were consistent with the view that non-bonded interactions in the methyl glycosides are relieved in the transition states for their interconversions.

  甲醇解反应的速率确定了D-木糖、D-阿拉伯糖、D-来苏糖和D-核糖的速率。发现戊糖的甲醇解反应通过四个可区分的、竞争性反应达到平衡：(1)戊糖→呋喃糖苷；(2)呋喃糖苷的异构化；(3)呋喃糖苷→吡喃糖苷；(4)吡喃糖苷的异构化。平衡时的糖苷组成是根据每种糖的四种糖苷的稳定性来解释的，这种稳定性受到立体和离子效应的影响；提出了呋喃糖苷环的构象分析方法。吡喃糖苷异构化反应的自由能变化与先前报道的吡喃环相互作用能计算出的值非常一致。这些反应的相对速率与这种观点相符，即在甲基糖苷的过渡态中，非键合相互作用得到了缓解。
• Conversion of d-xylose to protected d-lyxose derivatives and to d-lyxose, via the corresponding 1,2-anhydride
  作者：Velimir Popsavin、Sanja Grabež、Biljana Stojanović、Mirjana Popsavin、Vjera Pejanović、Dušan Miljković

  DOI：10.1016/s0008-6215(99)00164-0

  日期：1999.9

  hydrolysis of 3,5-di- O -benzyl-1,2- O -cyclohexylidene-α- d -xylofuranose gave the corresponding lactol, which was subsequently converted to the 3,5-di- O -benzyl-2- O -mesyl- d -xylofuranose. This compound readily reacted with sodium methoxide, sodium benzylate or sodium hydroxide (presumably via the corresponding 1,2-anhydride) to give the protected d -lyxofuranosides. These compounds were finally

  摘要对3,5-二-O-苄基-1,2-O-环己叉基-α-d-木呋喃糖进行酸水解得到相应的内酯，随后将其转化为3,5-二-O-苄基-2- O-甲磺酰基-d-木呋喃糖。该化合物容易与甲醇钠，苄基钠或氢氧化钠反应（大概通过相应的1,2-酐），得到保护的d-呋喃呋喃糖苷。这些化合物最终被转化为甲基α-d-lyxopyranoside或d-lyxose。
• Intramolecular 1,8-Hydrogen Atom Transfer Reactions in Disaccharide Systems Containing Furanose Units
  作者：Sabrina Guyenne、Elisa I. León、Angeles Martín、Inés Pérez-Martín、Ernesto Suárez

  DOI：10.1021/jo301153u

  日期：2012.9.7

  A previously developed 1,8-hydrogen atom transfer (HAT) reaction promoted by 6-O-yl alkoxyl radicals between the two pyranose units in Hexp-(1→4)-Hexp disaccharides has been extended to other systems containing at least a furanose ring in their structures. In Penf-(1→3)-Penf (A) and Hexp-(1→3)-Penf (B) disaccharides, the 1,8-HAT reaction and concomitant cyclization to a 1,3,5-trioxocane ring are in

  以前开发的由Hex p-（1→4）-Hex p二糖中两个吡喃糖单元之间的6- O-烷基烷氧基所促进的1,8-氢原子转移（HAT）反应已扩展到至少包含至少在其结构中有呋喃糖环。在Pen f-（1→3）-Pen f（A）和Hex p-（1→3）-Pen f（B）二糖，1,8-HAT反应和伴随的环化成1,3,5-三氧杂环丁烷环与C4–C5键的自由基β断裂和脱同源产物的形成竞争。使用四种可能的d-呋喃糖酶异构体研究了立体电子β-氧效应对β-断裂的影响，进而对1,8-HAT反应的影响。d -木糖-和d -来苏-衍生物给予优先1,8-HAT产品，而d -阿拉伯-和d -核糖-衍生物给烃氧基专门直接β-断裂。当6- O如在Pen f-（1→4）-Hex p（C）中所出现的，吡喃糖基团在吡喃糖环上显示出仅提供环化产物。
• Supramolecular Capsule-Catalyzed Highly β-Selective Furanosylation Independent of the S_N1/S_N2 Reaction Pathway
  作者：Tian-Ren Li、GiovanniMaria Piccini、Konrad Tiefenbacher

  DOI：10.1021/jacs.2c13641

  日期：——

  investigations indicated that the furanosylation mechanism is shifted toward an SN1 reaction on the mechanistic continuum between the prototypical SN1 and SN2 substitution types, as compared to the pyranosylation reaction inside the same catalyst. This is especially true for the lyxosyl donor, as indicated by the nucleophile reaction order of 0.26, and supported by metadynamics calculations. The mechanistic

  间苯二酚[4]芳烃胶囊被发现可催化多种不同呋喃糖基供体的β-选择性呋喃糖基化反应：α- d-和α- l-阿拉伯糖基-、α -l-岩藻糖基-、α -d-核糖基-、 α- d-木糖基-，甚至α- d-来木糖基氟化物。范围仅受封闭胶囊催化剂内部固有的有限体积的限制。该催化剂易于获得100克以上的规模，并且可以回收至少七轮，而不会显着损失活性、产率和选择性。机理研究表明，与同一催化剂内的吡喃基化反应相比，呋喃基化机理在原型S N 1 和S N 2 取代类型之间的机械连续体上转向S N 1 反应。对于来苏糖基供体来说尤其如此，如亲核反应级数 0.26 所示，并得到元动力学计算的支持。向 S N 1 的机械转变备受关注，因为它表明该催化剂不仅能够独立于底物构型进行 β-选择性呋喃糖基化和吡喃糖基化，而且还能够独立于操作机制。据我们所知，没有可替代的催化剂能够显示出这种特性。
• HPLC Analysis of the Product Distribution in the Iodine-Catalyzed Methyl Glycosidation of Pentoses and 6-Deoxyhexoses
  作者：Gyöngyi Gyémánt、András Lipták

  DOI：10.1080/07328309808002897

  日期：1998.4

  The product distribution of the iodine-catalyzed methyl glycosidation of four pentoses (D-ribose, D-arabinose, D-xylose, and D-lyxose) and two 6-deoxyhexoses (L-rhamnose, and D-fucose) was studied by HPLC using an APS column (dihydrogen sulphate form) with different acetonitrile-water mobile phases. In agreement with earlier results, a temperature dependent on-column isomerization was observed for all the investigated aldoses, except for ribose. The first-eluted furanosides were followed by pyranosides, and the free sugars were eluted last with the highest retention volumes.