methyl 2,3,4,6-tetra-O-methyl-β-D-galactopyranoside | 2296-47-1

• 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-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)tetrahydro-2H-pyran；(2R,3R,4S,5S,6R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane
• CAS: 2296-47-1
• 化学式: C₁₁H₂₂O₆
• 分子量: 250.292
• InChiKey: ZYGZAHUNAGVTEC-ZKKRXERASA-N

物化性质

• 保留指数：
  1458

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-β-D-galactopyranoside 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 生成 (R,R)-2,3-dimethoxy-succinic acid dimethyl ester
  参考文献：
  名称：

  Oxidation of completely methylated methyl glycopyranosides by chromic anhydride

  摘要：

  DOI：

  10.1007/bf01106666
• 作为产物：
  描述：

  (2R,3R,5R,6R)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol 生成 methyl 2,3,4,6-tetra-O-methyl-β-D-galactopyranoside
  参考文献：
  名称：

  DAmbra A. J., Gray G. R., Carbohydr. Res., 247 (1993) , S 299-303

  摘要：

  DOI：

文献信息

• TANNIN INHIBITORS OF HIV
  申请人：UNIVERSITY OF IOWA RESEARCH FOUNDATION

  公开号：US20130252909A1

  公开（公告）日：2013-09-26

  The invention provides a method to prevent or treat HIV-infection with synthetic tannins, and pharmaceutical compositions comprising synthetic tannins.

  这项发明提供了一种利用合成单宁预防或治疗HIV感染的方法，以及包含合成单宁的药物组合物。
• 1 : 1 Adduct Ion Formation of Permethylated Monosaccharides with Organic Cations in FAB Mass Spectrometry
  作者：Masami Sawada、Li Ouyang、Yoshio Takai、Hitoshi Yamada、Motohiro Shizuma、Takeshi Kinoshita、Tomoko Mochizuki、Terukiyo Hanafusa

  DOI：10.1246/bcsj.64.1243

  日期：1991.4

  the OCH3 configurational effects of M on (M+A)+ adduct ion formation. The findings can be interpreted in terms of multisite electrostatic interaction of oxygens with the cation. Coupled with the results of gas-phase behavior by FABMS/MS(CAD), solution behavior by 1H NMR, and model calculations by MNDO, the characteristic structure of the 1 : 1 adduct ion is deduced as host-guest type association between

  已在定量 FAB 质谱法中检查了一系列全甲基化单糖 (M; Ia–Ih) 和有机或金属阳离子 (A+) 之间 1:1 的加合离子形成。在相同 FABMS 条件下的仔细比较中，相对 (M+A)+ 峰强度以单糖的以下顺序增加，并进一步以几乎相同的程度增加，尽管使用了三种不同的阳离子，例如辛基铵，（甲氧基羰基） ) 甲基铵和钾离子：β-Glc<α-Glc<α-Gal<β-Gal≤α-Man<β-Man<α-Tal<β-Tal。顺序和阳离子独立性清楚地表明 OCH3 构型M 对 (M+A)+ 加合离子形成的影响。这些发现可以解释为氧与阳离子的多位点静电相互作用。
• Studies on the constituents of the root of Polygala tenuifolia Willdenow. II. On the structures of onjisaponins A, B and E.
  作者：SEIICHI SAKUMA、JUNZO SHOJI

  DOI：10.1248/cpb.30.810

  日期：——

  The structures of three triterpenoidal saponins, onjisaponins A (1), B (2) and E (3), were determined on the basis of spectral and chemical evidence as presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-[β-D-apio-D-furanosyl (1→3)] [β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl}-3-O-(α-L-rhamnopyranosyl)-4-O-(4'-methoxy-cinnamoyl)-β-D-fucopyranoside, presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-[β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl]-3-O-(α-L-rhamnopyranosyl)-4-O-(4'-methoxycinnamoyl)-β-D-fucopyranoside (=senegin III) and presenegenin- (3)-O-β-D-glucopyranosido-(28)-2-O-[β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl]-4-O-(3', 4', 5'-trimethoxycinnamoyl)-β-D-fucopyranoside, respectively. The 13C nuclear magnetic resonance spectra of onjisaponins A, B, E and their derivatives were investigated and each carbon signal was assigned as shown in Table I.

  三种三萜皂苷的结构，即翁鸡皂苷A（1）、B（2）和E（3），是基于光谱和化学证据确定的，其结构分别为：presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-[β-D-apio-D-furanosyl (1→3)] [β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl}-3-O-(α-L-rhamnopyranosyl)-4-O-(4'-methoxy-cinnamoyl)-β-D-fucopyranoside，presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-[β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl]-3-O-(α-L-rhamnopyranosyl)-4-O-(4'-methoxycinnamoyl)-β-D-fucopyranoside（=senegin III）和presenegenin-(3)-O-β-D-glucopyranosido-(28)-2-O-[β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl]-4-O-(3', 4', 5'-trimethoxycinnamoyl)-β-D-fucopyranoside。对翁鸡皂苷A、B、E及其衍生物的13C核磁共振光谱进行了研究，并对每个碳信号进行了如表I所示的赋值。
• Mechanism of anomerization of permethylated methyl d-glycopyranosides by trimethylsilyl trifluoromethanesulfonate
  作者：Chang Kiu Lee、Eun Ju Kim、In-Sook Han Lee

  DOI：10.1016/s0008-6215(98)00132-3

  日期：1998.7

  Abstract Anomerization of permethylated methyl d -glycopyranosides catalyzed by trimethylsilyl trifluoromethanesulfonate was examined by NMR spectroscopy and gas–liquid chromatography. The initial-rate analysis showed that the rates of anomerization of β to α were faster than those of the opposite at various concentrations of the catalyst. The overall rates of disappearance of the substrates were faster

  摘要用三氟甲磺酸三甲基甲硅烷基酯（NMR）和气相色谱法研究了全甲基化的甲基d-吡喃葡萄糖苷的三元甲硅烷基化反应。初始速率分析表明，在不同的催化剂浓度下，β到α的异化速率要快于相反的速率。底物的总消失速率比相反的端基异构体的出现速率快，这是因为形成了yl型化合物。后者的结构是基于1 H和13 C NMR光谱提出的，尽管它是不可分离的。环状和无环的氧鎓离子似乎都是异构化的中间体。前者似乎是形成吡啶型化合物以及α-糖苷键的异构化的关键中间体。
• Monosaccharide permethylation products for gas chromatography - mass spectrometry: how reaction conditions can influence isomeric ratios
  作者：Daniel Derbie Asres、Hélène Perreault

  DOI：10.1139/v97-166

  日期：1997.10.1

  Methylation analysis has been widely used for determination of carbohydrate structures by mass spectrometry. Permethylation of monosaccharides yields mixtures of anomeric pyranosides and furanosides. This paper discusses the influence of some of the permethylation reaction parameters on the proportions of isomeric products obtained. The ratios of three five- and six-membered ring products obtained

  甲基化分析已广泛用于通过质谱法测定碳水化合物的结构。单糖的全甲基化产生异头吡喃糖苷和呋喃糖苷的混合物。本文讨论了一些全甲基化反应参数对所得异构产物比例的影响。从两种全甲基化单糖 D-半乳糖和 L-岩藻糖获得的三个五元和六元环产物的比率已确定为反应参数的函数。Ciucanu 和 Kerek (1) 的方法（在氢氧化钠 (NaOH) 存在下的二甲基亚砜 (DMSO) 中的甲基碘）用作起点。“常规”方法包括将所有试剂与底物混合并在搅拌下进行反应。在这些条件下，D-半乳糖和 L-岩藻糖都产生了两种主要的全甲基化异构体，呋喃糖苷和吡喃糖苷，以及其他两种次要的异构体成分。我们研究了效果...