methyl-2,3,4,6-tetra-O-methyl-D-glucopyranoside | 4117-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-2,3,4,6-tetra-O-methyl-D-glucopyranoside
• 英文别名: methyl 2,3,4,6-tetra-O-methylglucopyranoside；(3R,4S,5R,6R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane
• CAS: 4117-96-8
• 化学式: C₁₁H₂₂O₆
• 分子量: 250.292
• InChiKey: ZYGZAHUNAGVTEC-YBTJCZCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl-2,3,4,6-tetra-O-methyl-D-glucopyranoside 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 41.17h， 生成 (D)-2,3,4,5,6-Penta-O-methyl-1-O-(triphenylmethyl)glucitol
  参考文献：
  名称：

  Noe, Christian R.; Knollmueller, Max; Ettmayer, Peter, Liebigs Annalen der Chemie, 1991, # 5, p. 417 - 424

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 、 甲醇 、 lithium aluminium tetrahydride 、 silver carbonate 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 methyl-2,3,4,6-tetra-O-methyl-D-glucopyranoside
  参考文献：
  名称：

  Saponin and sapogenol. XXXII. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (2). Azukisaponins I,II,III, and IV.

  摘要：

  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。

  DOI：

  10.1248/cpb.31.674

文献信息

• Studies on the constituents of Clematis species. III. On the saponins of the root of Clematis chinensis Osbeck.
  作者：HARUHISA KIZU、TSUYOSHI TOMIMORI

  DOI：10.1248/cpb.28.3555

  日期：——

  Four triterpenoid prosapogenins named CP2b, CP3b, CP9 and CP10 were isolated from the alkaline hydrolysate of the crude saponin obtained from the root of Clematis chinensis OSBECK. On the basis of chemical and physicochemical evidence, they were characterized as follows : CP2b (I), oleanolic acid 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinopyranoside ; CP3b (IV), hederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP9 (V), oleanolic acid 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP10 (X), hederagenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside.

  从金线莲根部的粗皂苷的碱水解产物中分离得到四个三萜原皂苷元,命名为CP2b、CP3b、CP9和CP10。根据化学和物理化学证据,它们被鉴定为:CP2b(I),齐墩果酸3-O-β-D-吡喃木糖基-(1→2)-α-L-吡喃阿拉伯糖苷;CP3b(IV),常春藤苷元3-O-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷;CP9(V),齐墩果酸3-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃核糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷;CP10(X),常春藤苷元3-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃核糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷。
• Saponin and sapogenol. XXXVIII. Structure of soyasaponin A2, 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.33.598

  日期：——

  Two new bisdesmosides of soyasapogenol A (1), named soyasaponin A1 and soyasaponin A2 (7), were isolated from soybean, the seeds of Glycine max MERRILL, together with the known soyasaponins I (4), II (5), and III (6). By employing a photochemical degradation method, which is a selective cleavage method for the glucuronide linkage in oligoglycosides, and on the bases of spectral analyses and chemical reactions, the structure of soyasaponin A2 was elucidated as 3-O-[β-D-galactopyranosyl (1→2)-β-D-glucuronopyranosyl]-22-O-[β-D-glucopyranosyl (1→3)-α-L-arabinopyranosyl] soyasapogenol A (7).

  从大豆（Glycine max MERRILL的种子）中分离出两种新的大豆皂醇A（1）的双糖苷，命名为大豆皂苷A1和大豆皂苷A2（7），以及已知的大豆皂苷I（4）、II（5）和III（6）。通过采用光化学降解方法，这是一种针对寡糖苷中葡萄糖醛酸键的选择性断裂方法，并基于光谱分析和化学反应，确定了大豆皂苷A2的结构为3-O-[β-D-半乳糖吡喃糖基（1→2）-β-D-葡萄糖醛酸吡喃糖基]-22-O-[β-D-葡萄糖吡喃糖基（1→3）-α-L-阿拉伯糖吡喃糖基]大豆皂醇A（7）。
• The structure of prosapogenin obtained from the saponin of Gleditsia japonica
  作者：Takao Konoshima、Hiroyuki Fukushima、Hideo Inui、Keiko Sato、Tokunosuke Sawada

  DOI：10.1016/0031-9422(81)85233-8

  日期：1981.1

  Abstract Prosapogenin was obtained by alkaline hydrolysis of Gleditsia saponin GS-C (echinoeystic acid 3, 28-O-bisdesmoside), a new triterpenoid saponin isolated from Gleditsia japoinica. Prosapogenin was shown on the basis of chemical and physicochemical data to be echinocystic acid 3-O-β- d -xylopyranosyl-(1–2)-α- l -arabinopyranosyl-(1–6)-β- d -glucopyranoside.

  摘要 Prosapogenin 是通过皂苷 GS-C（棘皮酸 3, 28-O-bisdesmoside）碱水解获得的，该皂苷是从皂角中分离得到的一种新的三萜皂苷。根据化学和物理化学数据显示，前皂苷元是棘囊酸 3-O-β-d-吡喃木糖基-(1-2)-α-l-阿拉伯吡喃糖基-(1-6)-β-d-吡喃葡萄糖苷。
• Studies on the constituents of Clematis species. IV. On the saponins of the root of Clematis chinensis Osbeck. IV.
  作者：HARUHISA KIZU、TSUYOSHI TOMIMORI

  DOI：10.1248/cpb.30.859

  日期：——

  Four triterpenoid prosapogenins named CP7a, CP8a, CP9a and CP10a have been isolated from the alkaline hydrolysate of the crude saponin obtained from the root of Clematis chinensis OSBECK. On the basis of chemical and physicochemical evidence, they were characterized as follows : CP7a (I), oleanolic acid 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP8a (VI), hederagenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP9a (XI), oleanolic acid 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP10a (XIII), hederagenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside.

  从以威灵仙根部的粗皂苷经过碱性水解后的水解产物中，分离得到了4个三萜皂苷元，分别命名为CP7a、CP8a、CP9a和CP10a。基于化学和物理化学证据，它们被鉴定如下：CP7a（I）为齐墩果酸3-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷；CP8a（VI）为常春藤苷元3-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷；CP9a（XI）为齐墩果酸3-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷；CP10a（XIII）为常春藤苷元3-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷。
• 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）。