methyl 3,4-di-O-methylglucopyranoside | 53956-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-methylglucopyranoside
• 英文别名: (3R,4R,5R,6R)-6-(hydroxymethyl)-2,4,5-trimethoxyoxan-3-ol
• CAS: 53956-02-8
• 化学式: C₉H₁₈O₆
• 分子量: 222.238
• InChiKey: VRNUDRWCZNJISG-VARJHODCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-丁磺酸内酯 、 methyl 3,4-di-O-methylglucopyranoside 生成 methyl 2,6-di-O-(4'-fluorosulfonyl)butyl-3,4-di-O-methyl-α,β-D-glucopyranoside
  参考文献：
  名称：

  Determination of the substituent distribution in O-sulfonylbutyl-(1→4)-glucans

  摘要：

  A method has been developed to determine the distribution of substituents in the glucose units of sulfonylbutylethers of cyclomaltoheptaose (beta-cyclodextrin). This method involves hydrolysis of the glucosidic linkages, permethylation, formation of sulfonylchlorides and subsequent transformation to the permethylated sulfonylfluoride derivatives. The latter were thermostable and could be analyzed by GLC and identified by EI and CIMS. For confirmation, the 2-, 3-, and 6-O-substituted standard compounds were independently synthesized and characterized by NMR and GLC-MS. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00056-2
• 作为产物：
  描述：

  生成 methyl 3,4-di-O-methylglucopyranoside
  参考文献：
  名称：

  Koizumi, Kyoko; Utamura, Toshiko, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 2776 - 2784

  摘要：

  DOI：

文献信息

• Saponin and sapogenol. XXXIX. Structure of soyasaponin A1, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max Merrill.
  作者：ISAO KITAGAWA、MASAYUKI SAITO、TOSHIO TANIYAMA、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.33.1069

  日期：——

  Five bioactive triterpene-oligoglycosides, named soyasaponins I, II, III, A1 (3), and A2 (2), were isolated from soybean, the seeds of Glycine max MERRILL (Leguminosae). By employing a photochemical degradation method and a lead tetraacetate degradation method, which are two of four selective cleavage methods available for the glucuronide linkage in oligoglycosides, the structure of soyasaponin A1 was elucidated to be 3-O [β-D-glucopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucuronopyranosyl-22-O-[β-D-glucopyranosyl (1→3)-α-L-arabinopyranosyl]-soyasapogenol A (3).

  从豆科植物大豆（Glycine max Merrill）的种子中分离出五种具有生物活性的三萜类低聚糖苷，分别命名为大豆皂苷I、II、III、A1（3）和A2（2）。通过采用两种选择性裂解方法，即光化学降解法和四乙酸铅降解法（这是四种可用于低聚糖苷中葡萄糖醛酸连接的选择性裂解方法中的两种），阐明了大豆皂苷A1的结构为：3-O[β-D-葡萄吡喃糖基（1→2）-β-D-半乳吡喃糖基（1→2）-β-D-葡萄糖醛吡喃糖基]-22-O[β-D-葡萄吡喃糖基（1→3）-α-L-阿拉伯吡喃糖基]-大豆皂苷元A（3）。
• 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。
• Novel hydrolyzable tannins from Nuphar Japonicum DC.
  作者：Makoto Nishizawa、Takashi Yamagishi、Genichiro Nonaka、Itsuo Nishioka、Hideo Bando

  DOI：10.1248/cpb.30.1094

  日期：——

  Two gallotannins (I and II) and an ellagitannin (III) named nupharin A have been isolated from Nuphar japonicum DC. (Nymphaeaceae). On the basis of chemical and spectral evidence, the structures of I, II and III were characterized as 1, 2, 6-tri-O-galloyl-α-D-glucose, 1, 2, 3, 4, 6-penta-O-galloyl-α-D-glucose and 1, 2, 6-tri-O-galloyl-3, 4-(S)-hexahydroxydiphenoyl-α-D-glucose, respectively.

  从日本睡莲（Nuphar japonicum DC.，属于睡莲科）中分离出了两种没食子的鞣酸（I和II）和一种被称为nupharin A的榄仁鞣酸（III）。根据化学和光谱证据，I、II和III的结构分别被鉴定为1, 2, 6-三-O-没食子酸基-α-D-葡萄糖、1, 2, 3, 4, 6-五-O-没食子酸基-α-D-葡萄糖和1, 2, 6-三-O-没食子酸基-3, 4-(S)-六羟基二苯甲酮-α-D-葡萄糖。
• Saponin and sapogenol. XL. Structure of sophoraflavoside I, a bisdesmoside of soyasapogenol B, from Sophorae Radix, the root of Sophora flavescens Aiton.
  作者：MASAYUKI YOSHIKAWA、HUIKANG WANG、HIROSHI KAYAKIRI、TOSHIO TANIYAMA、ISAO KITAGAWA

  DOI：10.1248/cpb.33.4267

  日期：——

  A new bisdesmoside of soyasapogenol B (3), named sophoraflavoside I (2), was isolated together with soyasaponin I (1) from Sophorae Radix (Sophora flavescens AITON, root). By employing a photochemical cleavage method for the glucuronide linkage in 2 and on the bases of chemical reactions and spectral analyses, the structure of sophoraflavoside I has been determined to be 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucuronopyranosyl]-22-O-[β-D-glucopyranosyl (1→2)-α-L-arabinopyranosyl] soyasapogenol B (2).

  一种新的大豆皂苷B的双脱糖苷（3），命名为黄豆黄酮苷I（2），与大豆皂苷I（1）从菟丝子根（Sophora flavescens AITON，根）中分离出来。通过采用光化学裂解法处理2中的葡萄糖醛酸连接基，并基于化学反应和光谱分析，确定黄豆黄酮苷I的结构为3-O-[α-L-甘露糖吡喃糖（1→2）-β-D-半乳糖吡喃糖（1→2）-β-D-葡萄糖醛酸吡喃糖]-22-O-[β-D-葡萄糖吡喃糖（1→2）-α-L-阿拉伯吡喃糖] 大豆皂苷B（2）。
• Saponin and sapogenol. XXXII. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (2). Azukisaponins I,II,III, and IV.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.674

  日期：——

  Six oleanene-oligoglycosides named azukisaponins I (1), II (2), III (3), IV (4), V, and VI were isolated from azuki beans, the seeds of Vigna angularis (WILLD.) OHWI et OHASHI (Leguminosae). Among them, the structures of azukisaponins I, II, III, and IV were elucidated as 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] sophoradiol (1), 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] soyasapogenol B (2), 3-O[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl] azukisapogenol (3), and 3-O-(β-D-glucopyranosyl)-28-O-[β-D-glucopyranosyl (1→6)-β-D-glucuronopyranosyl] gypsogenic acid (4), respectively on the basis of chemical and physicochemical evidence.

  从赤小豆（Vigna angularis (WILLD.) OHWI et OHASHI (豆科) 的种子）中分离出六种名为赤小豆皂苷 I (1)、II (2)、III (3)、IV (4)、V和 VI 的烯烃醇寡糖苷。其中，赤小豆皂苷 I、II、III 和 IV 的结构分别阐明为 3-O-[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 番荔枝醇 (1)、3-O-[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 大豆皂苷醇 B (2)、3-O[β-D-吡喃葡萄糖（1→2）-β-D-葡萄糖醛酸吡喃] 赤小豆皂苷醇 (3)、以及 3-O-(β-D-吡喃葡萄糖)-28-O-[β-D-吡喃葡萄糖（1→6）-β-D-葡萄糖醛酸吡喃] 石膏酸 (4)，这些均是基于化学和物理化学证据的结果。