methyl 2,2',3,3'4,4'-hexa-O-methyl-β-gentiobioside | 37093-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,2',3,3'4,4'-hexa-O-methyl-β-gentiobioside
• 英文别名: methyl hepta-O-methyl-β-gentiobioside；methyl-[O²,O³,O⁴-trimethyl-O⁶-(tetra-O-methyl-β-D-glucopyranosyl)-β-D-glucopyranoside]；Methyl-[O²,O³,O⁴-trimethyl-O⁶-(tetra-O-methyl-β-D-glucopyranosyl)-β-D-glucopyranosid]；Methyl-；Methyl β-Gentiobiosid-per-O-methyl；Methyl β-cellobiosid-per-O-methyl
• CAS: 37093-69-9
• 化学式: C₂₀H₃₈O₁₁
• 分子量: 454.515
• InChiKey: UXOPDHZWKBJQBG-XSVWGIRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101.53
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  、 methyl 2,2',3,3'4,4'-hexa-O-methyl-β-gentiobioside 在 三氟化硼乙醚 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以53%的产率得到methyl O-(2,3,4,6-tetra-O-methyl-α-D-glucopyranosyl)-(1->4)-O-(2-O-acetyl-3,6-di-O-methyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-methyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  碱催化的全甲基化3-O-糖基-吡喃葡萄糖苷-2-uloses降解。

  摘要：

  在Svensson降解的改进中，通过Swern氧化形成否则带有4-O-糖基取代基的全甲基化的吡喃葡萄糖苷-2-ulose。然后用三乙胺进行碱催化消除，得到4-脱氧-3-O-甲基糖-3-烯吡喃糖基-2-葡萄糖端基化的寡糖，其中糖基取代基释放为还原糖，但没有进一步降解。轻度的酸水解导致不饱和糖残基的去除，从而整体解聚发生，而最初氧化的糖残基仅净损失。

  DOI：

  10.1016/s0008-6215(00)90533-0
• 作为产物：
  描述：

  (2S,6R)-4-methoxy-2-(methoxymethyl)-6-[[(2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-[[(2R,3R,4S,5R,6R)-3,4,5,6-tetramethoxyoxan-2-yl]methoxy]oxan-2-yl]methoxy]-2H-pyran-5-one 在 sodium tetrahydroborate 、 Amberlite IR-120 (H⁺) 、 水 作用下， 生成 methyl 2,2',3,3'4,4'-hexa-O-methyl-β-gentiobioside
  参考文献：
  名称：

  碱催化的全甲基化3-O-糖基-吡喃葡萄糖苷-2-uloses降解。

  摘要：

  在Svensson降解的改进中，通过Swern氧化形成否则带有4-O-糖基取代基的全甲基化的吡喃葡萄糖苷-2-ulose。然后用三乙胺进行碱催化消除，得到4-脱氧-3-O-甲基糖-3-烯吡喃糖基-2-葡萄糖端基化的寡糖，其中糖基取代基释放为还原糖，但没有进一步降解。轻度的酸水解导致不饱和糖残基的去除，从而整体解聚发生，而最初氧化的糖残基仅净损失。

  DOI：

  10.1016/s0008-6215(00)90533-0

文献信息

• Saponin and sapogenol. XXXIII. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (3). Azukisaponins V and VI.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.683

  日期：——

  The chemical structures of azukisaponins V (1) and VI (5), two of the six oligoglycosidic ingredients of total azukisaponin isolated from azuki beans, the seeds of Vigna angularis (WILLD.) OHWI et OHASHI (Leguminosae), were investigated. By means of photochemical degradation and chemical analyses, the structures of azukisaponins V and VI were elucidated to be 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl]-soyasapogenol B (1) and 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl]-29-O-[β-D-glucopyranosyl (1→6)-β-D-glucuronopyranosyl] azukisapogenol (5), respectively. Azukisaponin VI (5) is the first reported example of a 3, 29-bisdesmoside of an oleanene oligoglycoside.

  研究了从红豆（Vigna angularis (WILLD.) OHWI et OHASHI）中提取的总红豆皂苷的六种寡糖苷成分中的两种：红豆皂苷V（1）和VI（5）的化学结构。通过光化学降解和化学分析，阐明了红豆皂苷V和VI的结构分别为3-O-[α-L-鼠李糖吡喃基（1→2）-β-D-葡萄糖吡喃基（1→2）-β-D-葡萄糖醛酸吡喃基]-大豆皂苷醇B（1）和3-O-[β-D-葡萄糖吡喃基（1→2）-β-D-葡萄糖醛酸吡喃基]-29-O-[β-D-葡萄糖吡喃基（1→6）-β-D-葡萄糖醛酸吡喃基]红豆皂苷醇（5）。红豆皂苷VI（5）是首次报道的三、二十九双配糖体的鞘脂寡糖苷。
• Oligosaccharides Self-Assemble and Show Intrinsic Optical Properties
  作者：Yang Yu、Soeun Gim、Dongyoon Kim、Zohar A. Arnon、Ehud Gazit、Peter H. Seeberger、Martina Delbianco

  DOI：10.1021/jacs.8b11882

  日期：2019.3.27

  Self-assembling peptides and oligonucleotides have given rise to synthetic materials with several applications in nanotechnology. Aggregation of synthetic oligosaccharides into well-defined architectures has not been reported even though natural polysaccharides, such as cellulose and chitin, are key structural components of biomaterials. Here, we report that six synthetic oligosaccharides, ranging from dimers to hexamers, self-assemble into nanostructures of varying morphologies and emit within the visible spectrum in an excitation-dependent manner. Well-defined differences in chain length, monomer modification, and aggregation methods yield glycomaterials with distinct shapes and properties. The excitation-dependent fluorescence in a broad range within the visible spectrum illustrates their potential for use in optical devices and imaging applications. We anticipate that our systematic approach of studying well-defined synthetic oligosaccharides will form the foundation of our understanding of carbohydrate interactions in nature.
• The Separation and Identification of the Products of Hydrolysis and Alcoholysis of Methylated Disaccharides
  作者：George H. Coleman、Donald E. Rees、Robert L. Sundberg、Chester M. McCloskey

  DOI：10.1021/ja01219a009

  日期：1945.3
• Zemplen, Chemische Berichte, 1924, vol. 57, p. 698,702
  作者：Zemplen

  DOI：——

  日期：——
• Haworth; Wylam, Journal of the Chemical Society, 1923, vol. 123, p. 3120,3123
  作者：Haworth、Wylam

  DOI：——

  日期：——