p-methoxyphenyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside | 1418284-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: p-methoxyphenyl 4,6-O-benzylidene-2-O-benzyl-β-D-glucopyranoside
• CAS: 1418284-22-6
• 化学式: C₂₇H₂₈O₇
• 分子量: 464.515
• InChiKey: POESBIGZOCMTTA-BLQNYSDHSA-N

物化性质

• 熔点：
  150-153 °C
• 沸点：
  647.2±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 在 2,4,6-三甲基吡啶 、 甲醇 、 N-碘代丁二酰亚胺 、 palladium 10% on activated carbon 、 水 、 氢气 、 sodium methylate 、 溶剂黄146 、 硫脲 、 lanthanum(lll) triflate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 p-methoxyphenyl α-L-arabinopyranosyl(1→2)-α-L-rhamnopyranosyl(1→3)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of two trisaccharides related to the hepatoprotective phenylethanoids leonoside E and F isolated from Leonurus japonicus Houtt

  摘要：

  The chemical synthesis of two trisaccharides related to leonoside E and F is reported. The target oligosaccharides were prepared in the form of their p-methoxyphenyl glycosides using a common disaccharide acceptor. All reaction steps were high yielding (>80%) and the stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.014
• 作为产物：
  描述：

  、 溴甲苯 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以1.9 g的产率得到p-methoxyphenyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of two trisaccharides related to the hepatoprotective phenylethanoids leonoside E and F isolated from Leonurus japonicus Houtt

  摘要：

  The chemical synthesis of two trisaccharides related to leonoside E and F is reported. The target oligosaccharides were prepared in the form of their p-methoxyphenyl glycosides using a common disaccharide acceptor. All reaction steps were high yielding (>80%) and the stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.014

文献信息

• Synthesis of a Pentasaccharide and Neoglycoconjugates Related to Fungal α-(1→3)-Glucan and Their Use in the Generation of Antibodies to Trace<i>Aspergillus fumigatus</i>Cell Wall
  作者：Bozhena S. Komarova、Maria V. Orekhova、Yury E. Tsvetkov、Remi Beau、Vishukumar Aimanianda、Jean-Paul Latgé、Nikolay E. Nifantiev

  DOI：10.1002/chem.201404770

  日期：2015.1.12

  position and 3‐OH group, respectively. Their removal from shared blocks led to donors and acceptors that were used for the synthesis of pentasaccharides. Coupling of free α‐(1→3)‐pentaglucoside with biotin and bovine serum albumin (BSA) gave glycoconjugate tools for mycological studies. Immunization of mice with the BSA conjugate induced the generation of antibodies that recognize α‐(1→3)‐glucan on A

  烟曲霉细胞壁的α-（1→3）-葡聚糖片段3-氨基丙基α-（1→3）-五葡糖苷是通过块状方法合成的。带有立体定向6- O-苯甲酰基的单糖和二糖N-苯基三氟乙酰亚氨酸盐的应用对于立体选择性α-葡萄糖基化至关重要。在产品中，p‐甲氧基苯基和乙酰丙酰基分别用作异头位置和3-OH基团的正交保护基。它们从共有的嵌段中除去导致供体和受体被用于合成五糖。游离的α-（1→3）-五葡糖苷与生物素和牛血清白蛋白（BSA）的偶联为糖基结合物的真菌学研究提供了工具。用BSA偶联物免疫小鼠会诱导产生识别烟曲霉细胞壁上的α-（1→3）-葡聚糖的抗体，并区分其形态型。这一发现代表了诊断测试系统和疫苗的开发的第一步，该系统可以检测和抵抗这种威胁生命的病原体。
• An Efficient Synthesis of the Pentasaccharide Repeating Unit of Pseudomonas aeruginosa Psl Exopolysaccharide
  作者：Fruzsina Demeter、Margaret Dah-Tsyr Chang、Yuan-Chuan Lee、Anikó Borbás、Mihály Herczeg

  DOI：10.1055/s-0039-1690747

  日期：2020.3

  preparation of this pentasaccharide was first described by Boons et al. in a 34-step synthesis. Based on their work, we have developed a new and effective pathway for the synthesis of the repeating pentasaccharide unit of the Psl exopolysaccharide. We have succeeded in simplifying the synthesis of the l -rhamnose and the α-selective d -mannose building blocks. Furthermore, taking advantage of a chemoselective

  铜绿假单胞菌是一种形成生物膜的革兰氏阴性细菌，是导致危及生命的医院感染的主要原因。铜绿假单胞菌的多糖合成位点 (Psl) 胞外多糖是防御细菌生物膜层的关键成分，是抗性物种的有希望的治疗靶点。Psl 胞外多糖由重复的五糖单元构成，这些单元包含一个 α-和两个 β-甘露糖苷键，以及一个 l-鼠李糖和一个 d-葡萄糖部分。Boons 等人首先描述了这种五糖的制备。在 34 步合成中。基于他们的工作，我们开发了一种新的有效途径来合成 Psl 胞外多糖的重复五糖单元。我们成功地简化了 l-鼠李糖和 α-选择性 d-甘露糖构建块的合成。此外，利用基于化学选择性预激活的 β-甘露糖基化，我们直接制备了硫糖苷二糖供体，并将其用于下一个偶联反应中，无需进一步转化。对甲氧基苯基糖苷形式的五糖分 26 个步骤制备，适用于生物测试。
• Is an acyl group at O-3 in glucosyl donors able to control α-stereoselectivity of glycosylation? The role of conformational mobility and the protecting group at O-6
  作者：Bozhena S. Komarova、Maria V. Orekhova、Yury E. Tsvetkov、Nikolay E. Nifantiev

  DOI：10.1016/j.carres.2013.11.016

  日期：2014.1

  The stereodirecting effect of a 3-O-acetyl protecting group, which is potentially capable of the remote anchimeric participation, and other protecting groups in 2-O-benzyl glucosyl donors with flexible and rigid conformations has been investigated. To this aim, an array of N-phenyltrifluoroacetimidoyl and sulfoxide donors bearing either 3-O-acetyl or 3-O-benzyl groups in combination with 4,6-di-O-benzyl, 6-O-acyl-4-O-benzyl, or 4,6-O-benzylidene protecting groups was prepared. The conformationally flexible 3-O-acetylated glucosyl donor protected at other positions with O-benzyl groups demonstrated very low or no alpha-stereoselectivity upon glycosylation of primary or secondary acceptors. On the contrary, 3,6-di-O-acylated glucosyl donors proved to be highly alpha-stereoselective as well as the donor having a single potentially participating acetyl group at O-6. The 3,6-di-O-acylated donor was shown to be the best alpha-glucosylating block for the primary acceptor, whereas the best alpha-selectivity of glycosylation of the secondary acceptor was achieved with the 6-O-acylated donor. Glycosylation of the secondary acceptor with the conformationally constrained 3-O-acetyl-4,6-O-benzylidene-protected donor displayed under standard conditions (-35 degrees C) even lower alpha-selectivity as compared to the 3-O-benzyl analogue. However, increasing the reaction temperature essentially raised the alpha-stereoselectivities of glycosylation with both 3-O-acetyl and 3-O-benzyl donors and made them almost equal. The stereodirecting effects of protecting groups observed for N-phenyltrifluoroacetimidoyl donors were also generally proven for sulfoxide donors. (C) 2013 Elsevier Ltd. All rights reserved.