methyl 2,3,6-tri-O-methyl-α,β-D-glucopyranoside | 51385-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-methyl-α,β-D-glucopyranoside
• 英文别名: 2,3,6-tri-O-methylglucose methyl pyranoside；methyl 2,3,6-tri-O-methyl-D-glucopyranoside；methyl-2,3,6-tri-O-methyl-D-glucopyranoside；methyl 2,3,6-tri-O-methyl-glucopyranoside；Methyl-2,3,6-tri-O-methyl-D-glykosid；Methyl-2,3,6-tri-O-methylglucoside；Methyl 2,3,6-tri-O-methylglucopyranoside；(2R,3R,4S,5R)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-ol
• CAS: 51385-14-9
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: WMAJFVGSEYZPMZ-ZKZCYXTQSA-N

物化性质

• 沸点：
  329.9±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 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：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-methyl-α,β-D-glucopyranoside 在 三甲基硅基甲烷磺酸酯 、 三氟化硼乙醚 吡啶 、 三乙基硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 D-Glucitol, 1,5-anhydro-2,3,6-tri-O-methyl-, propanoate
  参考文献：
  名称：

  Studies of model compounds for the analysis of ester-containing polysaccharides by the reductive-cleavage method

  摘要：

  The four O-propionyl regioisomers of methyl tri-O-methyl-alpha-D-glucopyranoside and the 2- and 3-O-propionyl regioisomers of methyl tri-O-methyl-beta-D-glucopyranoside were subjected to reductive cleavage in the presence of Et3SiH and Me3SiOSO2CF3, BF3.Et2O, or Me3SiOSO2Me-BF3.Et2O. The O-propionyl group was stable when either Me3SiOSO2CF3 or BF3.Et2O Was the catalyst, but was slowly reduced to the (1-propyl) ether when Me3SiOSO2Me-BF3.Et2O was the catalyst. Reductive cleavages catalyzed by Me3SiOSO2CF3 were complete in 6 h, those catalyzed by BF3.Et2O required at least 24 h, and those catalyzed by Me3SiOSO2Me-BF3.Et2O required 30 min or less. In the alpha-series, the rate of reductive cleavage decreased in the order 6-O-propionyl > 4-O-propionyl > 3-O-propionyl much greater than 2-O-propionyl. The reductive cleavage of beta-anomers was faster than that of the corresponding alpha-anomers. This effect was particularly striking for the alpha and beta-anomers of the 2-O-propionyl regioisomer, as would be expected on the basis of a participation reaction.

  DOI：

  10.1016/0008-6215(92)84021-j
• 作为产物：
  描述：

  甲醇 、 三甲基-Beta-环式糊精 在 乙酰氯 作用下， 反应 72.0h， 生成 methyl 2,3,6-tri-O-methyl-α,β-D-glucopyranoside
  参考文献：
  名称：

  Studies of model compounds for the analysis of ester-containing polysaccharides by the reductive-cleavage method

  摘要：

  The four O-propionyl regioisomers of methyl tri-O-methyl-alpha-D-glucopyranoside and the 2- and 3-O-propionyl regioisomers of methyl tri-O-methyl-beta-D-glucopyranoside were subjected to reductive cleavage in the presence of Et3SiH and Me3SiOSO2CF3, BF3.Et2O, or Me3SiOSO2Me-BF3.Et2O. The O-propionyl group was stable when either Me3SiOSO2CF3 or BF3.Et2O Was the catalyst, but was slowly reduced to the (1-propyl) ether when Me3SiOSO2Me-BF3.Et2O was the catalyst. Reductive cleavages catalyzed by Me3SiOSO2CF3 were complete in 6 h, those catalyzed by BF3.Et2O required at least 24 h, and those catalyzed by Me3SiOSO2Me-BF3.Et2O required 30 min or less. In the alpha-series, the rate of reductive cleavage decreased in the order 6-O-propionyl > 4-O-propionyl > 3-O-propionyl much greater than 2-O-propionyl. The reductive cleavage of beta-anomers was faster than that of the corresponding alpha-anomers. This effect was particularly striking for the alpha and beta-anomers of the 2-O-propionyl regioisomer, as would be expected on the basis of a participation reaction.

  DOI：

  10.1016/0008-6215(92)84021-j

文献信息

• 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。
• Synthesis of blockwise alkylated (1→4) linked trisaccharides as surfactants: influence of configuration of anomeric position on their surface activities
  作者：Atsushi Nakagawa、Hiroshi Kamitakahara、Toshiyuki Takano

  DOI：10.1016/j.carres.2011.04.034

  日期：2011.9

  alcoholysis of cellulose ethers and glycosylation of phenyl thio-cellobioside derivatives. Their surface activities in aqueous solution depended on their chemical structures: alpha- or beta-(1-->4) linkage between hydrophilic cellobiosyl and hydrophobic glucosyl blocks, methyl or ethyl groups of hydrophobic glucosyl block, and alpha- or beta-linked ether group at the C-1 of hydrophobic glucosyl block. The

  29/71（16））是通过组合方法合成的，包括酸催化纤维素醚的醇解和苯基硫代纤维二糖苷衍生物的糖基化。它们在水溶液中的表面活性取决于它们的化学结构：亲水性纤维二糖基和疏水性葡萄糖基嵌段之间的α-或β-（1→4）键，疏水性葡萄糖基嵌段的甲基或乙基以及α-或β-连接的醚疏水性葡糖基嵌段的C-1处的基团。还研究了α-和β-糖苷对表面活性的混合作用。结果，乙基β-d-吡喃葡萄糖基-（1-> 4）-α-d-吡喃葡萄糖基-（1-> 4）-2,3,6-tri-O-ethyl-ta-d-吡喃葡萄糖苷7（GβGαEβ）具有最高的表面活性，化合物7的临界胶束浓度（CMC）和γ（CMC）（在CMC处的表面张力）值分别为0.5mM（约0.03wt％）和34.5mN / m。除化合物9和10外，α-糖苷和β-糖苷混合物的表面张力几乎等于纯化合物的表面张力。没有纯化过程的α-糖苷和β-糖苷混合物的合成比纯化合物更容易
• Triterpene glycosides from Schefflera octophylla
  作者：T.V. Sung、W. Steglich、G. Adam

  DOI：10.1016/0031-9422(91)83647-4

  日期：1991.1

  3-epi-betulinic acid, three triterpene glycosides were isolated from leaves of Schefflera octophylla. The structures of the glycosides have been determined as 28-O-[alpha-L-rhamnopyranosyl(1----4)-O-beta-D-glucopyranosyl(1----6)-be ta-D- glucopyranosides of 3 alpha-hydroxy-lup-20(29)-ene-23,28-dioic acid, 3 alpha,11 alpha- dihydroxy-lup20(29)-ene-23,28-dioic acid and 3-epi-betulinic acid by spectroscopic

  除了 3-epi-桦木酸外，还从鹅掌楸叶中分离出三种三萜糖苷。已确定糖苷的结构为 28-O-[α-L-吡喃鼠李糖基(1----4)-O-β-D-吡喃葡萄糖基(1----6)-be ta-D-吡喃葡萄糖苷3 alpha-hydroxy-lup-20(29)-ene-23,28-dioic acid, 3 alpha,11 alpha-dihydroxy-lup20(29)-ene-23,28-dioic acid and 3-epi-betulinic acid通过光谱数据和化学转化。最后两种化合物首次在植物界被发现。
• Tanaka, Nobutoshi; Sada, Takuro; Murakami, Takao, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 2, p. 490 - 496
  作者：Tanaka, Nobutoshi、Sada, Takuro、Murakami, Takao、Saiki, Yasuhisa、Chen, Chiu-Ming

  DOI：——

  日期：——
• Melongoside L and melongoside M, steroidal saponins from Solanum melongena seeds
  作者：Pavel K. Kintia、Stepan A. Shvets

  DOI：10.1016/s0031-9422(00)80843-2

  日期：1985.1