methyl 2,4,6-tri-O-methyl-α,β-D-glucopyranoside | 53955-97-8

• 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,β-D-glucopyranoside
• 英文别名: methyl glycoside of 2,4,6-tri-O-methylglucose；methyl 2,4,6-tri-O-methyl-D-glucopyranoside；methyl 2,4,6-tri-O-methylglucopyranoside；methyl 2,4,6-tri-O-Me-glucopyranoside；methyl 2,4,6-tri-O-methyl-D-glucoside；Methyl-2,4,6-tri-O-methyl-D-glykosid；(3R,4S,5S,6R)-2,3,5-trimethoxy-6-(methoxymethyl)oxan-4-ol
• CAS: 53955-97-8
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: HJHDQMLCKFWWDV-QWIPYHCPSA-N

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,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， 反应 0.5h， 生成 D-Glucitol, 1,5-anhydro-2,4,6-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：

  (2S,3R,4S,5S,6R)-4-(benzyloxy)-2,3,5-trimethoxy-6-(methoxymethyl)tetrahydro-2H-pyran 在 palladium on activated charcoal 氢气 作用下， 生成 methyl 2,4,6-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

• Structural analysis of novel kestose isomers isolated from sugar beet molasses
  作者：Norio Shiomi、Tatsuya Abe、Hiroto Kikuchi、Tsutomu Aritsuka、Yusuke Takata、Eri Fukushi、Yukiharu Fukushi、Jun Kawabata、Keiji Ueno、Shuichi Onodera

  DOI：10.1016/j.carres.2016.02.002

  日期：2016.4

  GC-FID and GC-MS analyses of methyl derivatives, MALD-TOF-MS measurements and NMR spectra were used to confirm the structural characteristics of the isomers. The (1)H and (13)C NMR signals of each isomer saccharide were assigned using COSY, E-HSQC, HSQC-TOCSY, HMBC and H2BC techniques. These kestose isomers were identified as α-D-fructofuranosyl-(2- > 2)-α-D-glucopyranosyl-(1 < ->2)-β-D-fructofuranoside

  通过碳-塞利特柱色谱法和HPLC从甜菜糖蜜中分离出八种Kestose异构体。甲基衍生物的GC-FID和GC-MS分析，MALD-TOF-MS测量和NMR光谱用于确认异构体的结构特征。使用COSY，E-HSQC，HSQC-TOCSY，HMBC和H2BC技术分配每种异构体糖的（1）H和（13）C NMR信号。这些异构体被鉴定为α-D-果糖呋喃糖基-（2-> 2）-α-D-吡喃葡萄糖基-（1 <-> 2）-β-D-果糖呋喃糖苷，α-D-果糖呋喃糖基-（2-> 3 ）-β-D-果糖呋喃糖基-（2 <-> 1）-α-D-吡喃葡萄糖苷，α-D-果糖呋喃糖基-（2-> 4）-β-D-果糖呋喃糖基-（2 <-> 1）-α -D-吡喃葡萄糖苷，β-D-果呋喃糖基-（2-> 4）-β-D-呋喃呋喃糖基-（2 <-> 1）-α-D-吡喃葡萄糖苷，β-D-呋喃呋喃糖基-（2-> 3） -α-D-吡喃葡萄糖基-（1
• The structures of six antifungal oligoglycosides, stichlorosides A1,A2,B1,B2,C1, and C2, from the sea cucumber Stichopus chloronotus (Brandt).
  作者：ISAO KITAGAWA、MOTOMASA KOBAYASHI、TATSUYA INAMOTO、TOHRU YASUZAWA、YOSHIMASA KYOGOKU

  DOI：10.1248/cpb.29.2387

  日期：——

  Chemical structures are reported for six antifungal lanostane-type triterpene-oligoglycosides from the Okinawan sea cucumber Stichopus chloronotus (BRANDT). The compounds are : stichlorosides A1 (9), B1 (15), C1 (20) [having stichlorogenol (3) as the aglycone] and A2 (10), B2 (16), C 2 (21) [dehydrostichlorogenol (4) as the aglycone].

  来自冲绳海参Stichopus chloronotus（Brandt）的六种抗真菌羊毛甾烷型三萜寡糖苷的化学结构已见报道。这些化合物分别是：stichloroside A1（9）、B1（15）、C1（20）[以stichlorogenol（3）为苷元]，以及A2（10）、B2（16）、C2（21）[以dehydrostichlorogenol（4）为苷元]。
• Structural investigation of Klebsiella K-type 4 capsular polysaccharide
  作者：Edwin H. Merrifield、Alistair M. Stephen

  DOI：10.1016/s0008-6215(00)84701-1

  日期：1981.10

  Klebsiella K4 contains the tetrasaccharide repeating-sequence leads to 3)-alpha-D-Glcp-(1 leads to 2)-alpha-D-Glcp A-(1 leads to 3)-alpha-D-Manp-(1 leads to 3)-beta-D-Glcp-(1 leads to. P.m.r. spectroscopy and the measurement of optical rotation were used to establish the anomeric linkages in the polysaccharide and in the oligosaccharides derived by partial hydrolysis. The repeating unit also contains one 0-acetyl

  克雷伯氏菌K4的荚膜多糖含有四糖重复序列，导致3）-α-D-Glcp-（1导致2）-α-D-GlcpA-（1导致3）-α-D-Manp- （1导致3）-β-D-Glcp-（1导致。Pmr光谱学和旋光度测量被用来建立多糖和部分水解衍生的寡糖中的异头键。重复单元还包含一个0-乙酰基。
• Konishi, Tenji; Narumi, Yoko; Watanabe, Kazuaki, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 10, p. 4155 - 4161
  作者：Konishi, Tenji、Narumi, Yoko、Watanabe, Kazuaki、Kiyosawa, Shiu、Shoji, Junzo

  DOI：——

  日期：——
• 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：——