methyl 2,4,6-tri-O-methyl-α-D-glucopyranoside | 35939-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4,6-tri-O-methyl-α-D-glucopyranoside
• 英文别名: Methyl-2,4,6-tri-O-methyl-α-D-glucopyranosid；(2S,3R,4S,5S,6R)-2,3,5-trimethoxy-6-(methoxymethyl)oxan-4-ol
• CAS: 35939-71-0
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: HJHDQMLCKFWWDV-ZOZBQHSOSA-N

物化性质

• 沸点：
  333.1±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 2,4,6-tri-O-methyl-α-D-glucopyranoside 在 三甲基硅基甲烷磺酸酯 、 三氟化硼乙醚 三乙基硅烷 、 dimsyl lithium 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 1,5-anhydro-2,4,6-tri-O-methyl-3-O-(1-propyl)-D-glucitol
  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：

  在 盐酸 、 silver(l) oxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl 2,4,6-tri-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  A furostanol glucuronide from Solanum lyratum

  摘要：

  DOI：

  10.1016/s0031-9422(00)80717-7

文献信息

• Studies on the constituents of Momordica cochinchinensis Spreng. II. Isolation and characterization of the root saponins, Momordins I, II and III.
  作者：MASAYO IWAMOTO、HIKARU OKABE、TATSUO YAMAUCHI

  DOI：10.1248/cpb.33.1

  日期：——

  From the root of Momordica cochinchinensis SPRENG. (Cucurbitaceae), three saponins named momordins I, II and III have been isolated. Their structures were determined on the basis of chemical and spectral evidence as oleanolic acid 3-O-α-L-arabinopyranosyl (1→3)-β-D-glucuronopyranoside (momordin I), 28-O-β-D-glucopyranoside of momordin I (momordin II) and 3β-hydroxy-11α, 12α-epoxy-olean-28, 13-olide 3-O-α-L-arabinopyranosyl (1→3)-β-D-glucuronopyranoside (momordin III). Momordin II was proved to be identical with hemsloside Ma1 isolated from the tubers of Hemsleya macrosperma and H. chinensis.

  从木鳖子（Momordica cochinchinensis SPRENG. 葫芦科）的根中分离出三种皂苷，命名为木鳖子苷I、II和III。它们的结构通过化学和光谱证据确定为：木鳖子苷I（3-O-α-L-阿拉伯吡喃糖基（1→3）-β-D-葡萄糖醛酸苷基的齐墩果酸）、木鳖子苷II（木鳖子苷I的28-O-β-D-葡萄糖苷）和木鳖子苷III（3β-羟基-11α, 12α-环氧-齐墩果-28, 13-内酯的3-O-α-L-阿拉伯吡喃糖基（1→3）-β-D-葡萄糖醛酸苷）。木鳖子苷II被证实与从大苞赤瓟和中华赤瓟块根中分离出的hemsloside Ma1相同。
• Defining oxyanion reactivities in base-promoted glycosylations
  作者：Martin Matwiejuk、Joachim Thiem

  DOI：10.1039/c1cc11690h

  日期：——

  Saccharide oxyanions obtained by base treatment could be employed in glycosylation to give oligosaccharides with high stereo- and regioselectivities.

  通过碱处理获得的糖类氧阴离子可用于糖基化以产生具有高立体选择性和区域选择性的寡糖。
• Regioselective methylation of methyl glycopyranosides with diazomethane in the presence of transition-metal chlorides and of boric acid
  作者：Evgeny V. Evtushenko

  DOI：10.1016/s0008-6215(99)00044-0

  日期：1999.3

  Abstract Partial methylation of the methyl pyranosides of a number of pentoses, hexoses, 6-deoxyhexoses, methyl uronates and their methyl ethers with diazomethane in the presence of transition-metal chlorides and boric acid was studied. It was found for methyl glycosides of pentoses and 6-deoxyhexoses that tin(II), antimony(III), and titanium(IV) chlorides as well as boric acid promoted substitution

  摘要研究了在过渡金属氯化物和硼酸存在下，许多戊糖，己糖，6-脱氧己糖，尿酸甲酯及其甲基醚的甲基吡喃糖苷与重氮甲烷的部分甲基化。发现戊糖和6-脱氧己糖的甲基糖苷中锡（II），锑（III）和钛（IV）氯化物以及硼酸主要促进OH-3的取代，但被铈（III）和锌的取代（II）观察到盐主要取代了OH-2。在所有情况下，甲基β-1-鼠李糖吡喃糖苷的甲基化表现出较高的OH-2反应性。在氯化锡（II），锑（III）和铈（III）的存在下，己糖甲基糖苷的甲基化反应主要产生了3-甲基醚。不参与进一步络合的3-甲基醚 积聚高达50-80％的反应混合物（95％至100％的单甲醚馏分）。建议用于许多糖的方便的甲基醚的合成。
• New Method for Regioselective Glycosylation Employing Saccharide Oxyanions
  作者：Martin Matwiejuk、Joachim Thiem

  DOI：10.1002/ejoc.201100861

  日期：2011.10

  As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl-α-D-glucopyranosides were

  作为糖基化的替代概念，研究了先激活受体羟基以形成选择性糖苷键，以得到复杂的寡糖。从部分保护的糖类中获得的氧阴离子通过使用吡喃糖基卤化物进行糖基化，并研究了区域化学结果。最初，部分甲基化的甲基-α-D-吡喃葡萄糖苷被用作模型系统来研究碱基促进糖基化的基本机制原理。实现了高区域选择性和立体特异性糖苷键的形成，并且该方法的范围通过不同的全苄化糖基供体进行了扩展。
• The steroidal glycosides of the flowers of Yucca gloriosa
  作者：Kimiko Nakano、Emi Matsuda、Kaori Tsurumi、Tokushi Yamasaki、Kotaro Murakami、Yoshihisa Takaishi、Toshiaki Tomimatsu

  DOI：10.1016/0031-9422(88)80033-5

  日期：1988.1

  Abstract Four steroidal compounds were isolated from the fresh flowers of Yucca gloriosa and their structures were elucidated as tigogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, gitogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, gitogenin 3-O-α- l -rhamnopyranosyl-β-lycotetraoside and proto-type of gitogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, on the basis of physical and chemical investigations

  摘要 从兰兰鲜花中分离得到4种甾体化合物，并阐明了其结构为：tigogenin 3-O-β-d-吡喃木糖基-β-lycotetraoside、gitogenin 3-O-β-d-xylopyranosyl-β-lycotetraoside、gitogenin 3-O-α-l -rhamnopyranosyl-β-lycotetraoside 和 gitogenin 3-O-β-d -xylopyranosyl-β-lycotetraoside 的原型，基于物理和化学研究。