methyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside | 34820-00-3

• 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-β-D-galactopyranoside
• 英文别名: methyl-2,3,4,6-tetra-O-benzoyl-β-D-galactoside；methyl tetra-O-benzoyl-β-D-galactopyranoside；[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 34820-00-3
• 化学式: C₃₅H₃₀O₁₀
• 分子量: 610.617
• InChiKey: OSFLTUBNBXWBHG-XFUYZNCPSA-N

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-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 水 、 磷脂酶B 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and Structure Elucidation of Benzoylated Deoxyfluoropyranosides

  摘要：

  Benzoylated deoxyfluoropyranosides have been synthesized, starting with protected, unprotected, or fluorinated precursors. Fluorination of eight derivatives was compared using DAST and Deoxo-Fluor as reagents. Deoxo-Fluor was found to be especially useful in the fluorination of methyl 2,3,4-O-tribenzoyl -D-mannopyranoside and -D-glucopyranoside, resulting in better yields and avoiding the 1,6-methoxy migration experienced with DAST for one derivative. The two reagents gave comparable yields in the fluorination of other methyl pyranosides, confirming Deoxo-Fluor as a safer alternative to DAST. Methyl -D-mannopyranoside underwent fluorination to yield the 4,6-difluorotalopyranoside and the corresponding cyclic sulfite. The NMR spectroscopic properties of 11 benzoyl deoxy-fluoropyranosides are reported.

  DOI：

  10.1080/07328303.2010.540055
• 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-β-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
• Amphiceramide A and B, Novel Glycosphingolipids from the Marine Sponge<i>Amphimedon compressa</i>
  作者：Valeria Costantino、Ernesto Fattorusso、Concetta Imperatore、Alfonso Mangoni、Roberta Teta

  DOI：10.1002/ejoc.200801230

  日期：2009.5

  sponge Amphimedon compressa has shown it to contain two novel glycosphingolipids, amphiceramide A (1a) and B (2a), which possess an unusual Δ6-phytosphingosine. The saccharide chain of amphiceramide A is composed of a β-glucose residue glycosylated at the 6-position by an N-acetyl-β-glucosamine and has never been found before in a natural product. The saccharide chain of amphiceramide B consists of an

  加勒比海绵 Amphimedon compressa 的糖脂分析表明，它含有两种新型鞘糖脂，两性神经酰胺 A (1a) 和 B (2a)，它们具有不寻常的 Δ6-植物鞘氨醇。两性神经酰胺 A 的糖链由 6 位被 N-乙酰基-β-葡糖胺糖基化的 β-葡萄糖残基组成，以前从未在天然产物中发现过。两性神经酰胺 B 的糖链由异乳糖 [Gal(1β6)Glc] 残基 β-连接到神经酰胺组成，这是首次在天然糖鞘脂中发现。此外，海绵含有一种新的分子种类，乙酰氨基葡萄糖神经酰胺 (3a)，以及已知的葡萄糖神经酰胺 4a (halicerebroside A) 和蜜二糖神经酰胺 5a (amphimelibioside C)。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• 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。
• A Carbohydrate-Anion Recognition System in Aprotic Solvents
  作者：Bo Ren、Hai Dong、Olof Ramström

  DOI：10.1002/asia.201301617

  日期：2014.5

  A carbohydrate–anion recognition system in nonpolar solvents is reported, in which complexes form at the B‐faces of β‐D‐pyranosides with H1‐, H3‐, and H5‐cis patterns similar to carbohydrate–π interactions. The complexation effect was evaluated for a range of carbohydrate structures; it resulted in either 1:1 carbohydrate–anion complexes, or 1:2 complex formation depending on the protection pattern

  报道了一种在非极性溶剂中的碳水化合物-阴离子识别系统，其中在 β- D-吡喃糖苷的 B 面形成复合物，其H1-、H3-和 H5-顺式模式类似于碳水化合物-π 相互作用。对一系列碳水化合物结构的络合效应进行了评估；根据碳水化合物的保护模式，它导致 1:1 碳水化合物 - 阴离子复合物或 1:2 复合物形成。还用不同的阴离子和溶剂评估了相互作用。在这两种情况下，它都导致了显着的结合差异。结果表明络合源于范德华相互作用或弱 CH ⋅⋅⋅ A − 结合配偶体之间的氢键，与碳水化合物的吸电子基团以及阴离子的氢键接受能力增加有关。
• 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.