methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranoside | 14315-82-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranoside
• 英文别名: methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl；α-methyl-2,3,4,6-tetra-O-benzoyl-D-galactose；methyl tetra-O-benzoyl-α-D-galactopyranoside；Methyl-；Methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosid；Methyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosid；methyl 2,3,4,6-tetra-O-benzoyl-alpha-d-galacto-pyranoside；[(2R,3S,4S,5R,6S)-3,4,5-tribenzoyloxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 14315-82-3
• 化学式: C₃₅H₃₀O₁₀
• 分子量: 610.617
• InChiKey: OSFLTUBNBXWBHG-UQPXDNIZSA-N

物化性质

• 沸点：
  725.1±60.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranoside 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 以100%的产率得到Α-D-乳酸吡喃糖苷甲酯
  参考文献：
  名称：

  受端粒酶抑制剂阿奇诺糖苷A启发的硫酸化脂糖

  摘要：

  硫酸化的脂糖是端粒酶的已知抑制剂，在这里我们描述了一系列天然产物axinelloside A激发的一系列硫酸化的脂糖的合成，据报道，该产物可作为人类端粒酶的抑制剂。我们利用2-癸烯酸和硫酸咪唑鎓酯的一系列区域选择性酰化反应，建立了一种健壮且可扩展的半乳糖基脂糖合成路线。

  DOI：

  10.1016/j.tetlet.2017.11.038
• 作为产物：
  描述：

  Ectyoceramide hexaacetate 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranoside
  参考文献：
  名称：

  Ectyoceramide，第一种来自海洋海绵 Ectyoplasia ferox 的天然六呋喃基神经酰胺

  摘要：

  Ectyoceramide (1a) 是一种独特的单糖基神经酰胺，含有呋喃糖形式的半乳糖，是从 Ectyoplasia ferox 中分离出来的，其结构由核磁共振光谱、多重串联质谱和化学降解确定。胞外神经酰胺是单己呋喃糖基神经酰胺的第一个例子，更一般地说，是第一个含有呋喃糖形式的糖的天然鞘糖脂。(Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200390202

文献信息

• Regioselective C-6 Hydrolysis of Methyl<i>O</i>-Benzoyl-pyranosides Catalysed by<i>Candida Rugosa</i>Lipase
  作者：Aslan Esmurziev、Eirik Sundby、Bård Helge Hoff

  DOI：10.1002/ejoc.200801268

  日期：2009.4

  Hydrolysis of six methyl O-benzoyl-pyranosides has been investigated using Candida rugosa lipase in dioxane/buffer mixtures. The lipase catalysed the hydrolysis of all substrates in a regiospecific manner at C-6. The rate of reaction was dependent on pyranoside structure, reaction temperature and scale, dioxane concentration and agitation speed. Starting from their C-6 O-benzoyl precursors, the methyl

  六甲基邻苯甲酰基吡喃糖苷的水解作用已在二恶烷/缓冲液混合物中使用 Candida rugosa 脂肪酶进行了研究。脂肪酶以区域特异性方式在 C-6 处催化所有底物的水解。反应速率取决于吡喃糖苷结构、反应温度和规模、二恶烷浓度和搅拌速度。从它们的 C-6 O-苯甲酰基前体开始，α-D-半乳糖、β-D-半乳糖、α-D-葡萄糖和甲基 2,3 的甲基 2,3,4-三-O-苯甲酰基-吡喃糖苷-二-O-苯甲酰基-α-D-吡喃半乳糖苷可以以 85-96% 的产率分离。在水解甲基 2,3,4,6-四-O-苯甲酰-α-D-吡喃葡萄糖苷和甲基 2,3,4,6-四-O-苯甲酰-β-D-吡喃半乳糖苷底物时观察到抑制作用，其中部分可以通过增加反应体积来克服。甲基 2,3,4, 6-四-O-苯甲酰-β-D-吡喃葡萄糖苷和甲基2,3,4,6-四-O-苯甲酰-α-D-吡喃甘露糖苷是皱纹假丝酵母脂肪酶的不良底物，且产物转化
• Selective Deprotection of Fully Benzoylated Nucleoside Derivatives
  作者：Rachida Zerrouki、Vincent Roy、Amel Hadj‐Bouazza、Pierre Krausz

  DOI：10.1081/car-200030095

  日期：2004.12.27

  Selective deprotection of benzoylated hydroxyl groups is one of the crucial problems in the synthesis of nucleoside analogues as well as of other polyfunctional molecules.

  苯甲酰化羟基的选择性脱保护是核苷类似物以及其他多官能分子合成中的关键问题之一。
• ¹ H and ¹³ C NMR data of methyl tetra-<i>O</i> -benzoyl-<i>D</i> -pyranosides in acetone-<i>d</i> ₆
  作者：Aslan Esmurziev、Nebojša Simić、Eirik Sundby、Bård Helge Hoff

  DOI：10.1002/mrc.2400

  日期：2009.5

  Complete assignments of (1)H- and (13)C-NMR resonances of five methyl tetra-O-benzoyl-D-pyranosides based on (1)H, (13)C, 2D DQF-COSY, HMQC, HMBC and HSQC-TOCSY experiments have been performed.

  基于（1）H，（13）C，2D DQF-COSY，HMQC，HMBC和HSQC的五个甲基四-O-苯甲酰基-D-吡喃糖苷的（1）H-和（13）C-NMR共振的完全分配-TOCSY实验已经进行。
• Antiplasmodial Metabolites Isolated from the Marine Octocoral <i>Muricea austera</i>
  作者：Marcelino Gutiérrez、Todd L. Capson、Héctor M. Guzmán、José González、Eduardo Ortega-Barría、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1021/np060007f

  日期：2006.10.1

  Bioassay-guided fractionation of the MeOH extract from the octocoral Muricea austera collected in the Pacific coast of Panama led to the isolation of eight compounds, including three tyramine derivatives (1-3), two steroidal pregnane glycosides ( 4, 5), and three sesquiterpenoids (6-8). Compounds 2-5 are new natural products, and their structures were determined on the basis of their spectroscopic data (HRMS, 1D and 2D NMR, and CD studies). The antiprotozoal activities of the natural compounds 1-8 as well as those of a series of synthetic glycosides (11-22) and tyramine derivatives (23-35) were evaluated in vitro against a drug-resistant Plasmodium falciparum and intracellular form of Trypanosoma cruzi.
• Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase
  作者：Evangelina Repetto、Carla Marino、M. Laura Uhrig、Oscar Varela

  DOI：10.1016/j.bmc.2009.02.045

  日期：2009.4

  Thiodisaccharides having beta-D-Galf or alpha-L-Araf units as non-reducing end have been synthesized by the SnCl4- or MoO2Cl2-promoted thioglycosylation of per-O-benzoyl-D-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-alpha-L-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure beta-D-Galf(1 -> 6)-6-thio-alpha-D-Glcp-OMe (5) or beta-D-Galf(1 -> 6)-6-thio-alpha-D-Galp-OMe (15) were obtained. The respective alpha-L-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, beta-D-Galf(1 -> 4)-4-thio- 3-deoxy-alpha-L-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-beta-D-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the beta-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme. (c) 2009 Elsevier Ltd. All rights reserved.