p-methoxyphenyl α-L-arabinopyranoside | 96887-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl α-L-arabinopyranoside
• 英文别名: 4-methoxyphenyl α-L-arabinopyranoside；(2S,3R,4S,5S)-2-(4-methoxyphenoxy)oxane-3,4,5-triol
• CAS: 96887-44-4
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: VQIWAEGTXPEOHB-YFKTTZPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl α-L-arabinopyranoside 、 2,2-二甲氧基丙烷 在 D(+)-10-樟脑磺酸 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以91%的产率得到p-methoxyphenyl 3,4-O-isopropylidene-α-L-arabinopyranoside
  参考文献：
  名称：

  通过反应性调节来寡糖：从海洋海绵羊胎素中分离得到的甾体糖苷Sokodoside B的三糖的聚合合成

  摘要：

  据报道，从胎盘草中分离出的甾族糖苷Sokodoside B的三糖的化学合成。为了获得更好的结果，使用了通过使用固定在二氧化硅上的H 2 SO 4与N-碘代琥珀酰亚胺联用的硫糖苷活化来进行立体选择性，高产的糖基化策略。进行后期TEMPO介导的氧化，以形成所需的糖醛酸部分。还通过使用双糖基化方法制备了靶三糖的类似物。

  DOI：

  10.1016/j.tet.2007.09.072
• 作为产物：
  描述：

  L-(+)-arabinose 在 吡啶 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 p-methoxyphenyl α-L-arabinopyranoside
  参考文献：
  名称：

  Organoboron-Promoted Regioselective Glycosylations in the Synthesis of a Saponin-Derived Pentasaccharide from Spergularia ramosa

  摘要：

  Organoboron-mediated regioselective glycosylations were employed as key steps in the total synthesis of a branched pentasaccharide from a saponin natural product. The ability to use organoboron activation to differentiate OH groups in an unprotected glycosyl acceptor, followed by substrate-controlled reactions of the obtained disaccharide, enabled a streamlining of the synthesis relative to a protective group-based approach. This study revealed a matching/mismatching effect of the relative configuration of donor and acceptor on the efficiency of a regioselective glycosylation reaction, a problem that was solved through the development of a novel boronic acid-amine copromoter system for glycosyl acceptor activation.

  DOI：

  10.1021/acs.joc.5b00950

文献信息

• Catalytic Site-Selective Carbamoylation of Pyranosides
  作者：Jérôme Alsarraf、Lucas Petitpoisson、André Pichette

  DOI：10.1021/acs.orglett.1c02116

  日期：2021.8.6

  Carbamate-bearing carbohydrates contribute to the pharmacological properties of various natural glycosides. The catalytic site-selective carbamoylation of minimally protected pyranosides was achieved for the first time to bypass protection/deprotection sequences. 1-Carbamoylimidazoles were used as the carbamoylation reagents to circumvent the harmful and unstable phosgene and isocyanates. This borinic

  含氨基甲酸酯的碳水化合物有助于各种天然糖苷的药理特性。首次实现了最低限度保护的吡喃糖苷的催化位点选择性氨基甲酰化，以绕过保护/脱保护序列。1-氨基甲酰咪唑被用作氨基甲酰化试剂以规避有害且不稳定的光气和异氰酸酯。这种硼酸催化的转化使博来霉素和类似物的肿瘤细胞结合氨基甲酰甘露糖苷部分能够以 56% 至 89% 的产率获得。
• Concise synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum
  作者：Santanu Mandal、Balaram Mukhopadhyay

  DOI：10.1016/j.tet.2007.08.077

  日期：2007.11

  Chemical synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum is reported. Stereoselective, high-yielding glycosylation strategies were developed using H2SO4 immobilized on silica for activation of trichloroacetimidate donors, or in conjunction with N-iodosuccinimide for activation of a thioglycoside. A late stage TEMPO-mediated oxidation was performed for

  报道了从炭疽病菌中分离出的与皂苷有关的两种三糖的化学合成。使用固定在二氧化硅上的H 2 SO 4活化三氯乙酰亚氨酸酯供体，或与N-碘琥珀酰亚胺联用来活化硫糖苷，开发了立体选择性，高产糖基化策略。进行后期TEMPO介导的氧化，以形成所需的糖醛酸部分。
• Organoiridium complexes: efficient catalysts for the formation of sugar acetals and ketals
  作者：Soumik Mandal、Prashant Ranjan Verma、Balaram Mukhopadhyay、Parna Gupta

  DOI：10.1016/j.carres.2011.05.008

  日期：2011.9

  [Cp*IrCl2](2) is used as an efficient promoter for the synthesis of sugar acetals and ketals with good to excellent yields. The catalyst is found to be general for a wide range of sugars. (C) 2011 Elsevier Ltd. All rights reserved.
• Organoboron-Promoted Regioselective Glycosylations in the Synthesis of a Saponin-Derived Pentasaccharide from <i>Spergularia ramosa</i>
  作者：Ross S. Mancini、Corey A. McClary、Stefi Anthonipillai、Mark S. Taylor

  DOI：10.1021/acs.joc.5b00950

  日期：2015.9.4

  Organoboron-mediated regioselective glycosylations were employed as key steps in the total synthesis of a branched pentasaccharide from a saponin natural product. The ability to use organoboron activation to differentiate OH groups in an unprotected glycosyl acceptor, followed by substrate-controlled reactions of the obtained disaccharide, enabled a streamlining of the synthesis relative to a protective group-based approach. This study revealed a matching/mismatching effect of the relative configuration of donor and acceptor on the efficiency of a regioselective glycosylation reaction, a problem that was solved through the development of a novel boronic acid-amine copromoter system for glycosyl acceptor activation.
• Oligosaccharides through reactivity tuning: convergent synthesis of the trisaccharides of the steroid glycoside Sokodoside B isolated from marine sponge Erylus placenta
  作者：Somnath Dasgupta、Kausikisankar Pramanik、Balaram Mukhopadhyay

  DOI：10.1016/j.tet.2007.09.072

  日期：2007.12

  synthesis of the trisaccharide of the steroid glycoside Sokodoside B isolated from Erylus placenta is reported. Stereoselective, high-yielding glycosylation strategies through thioglycoside activation using H2SO4 immobilized on silica in conjunction with N-iodosuccinimide are used for better results. A late stage TEMPO-mediated oxidation was performed for the formation of required uronic acid moiety. An analog

  据报道，从胎盘草中分离出的甾族糖苷Sokodoside B的三糖的化学合成。为了获得更好的结果，使用了通过使用固定在二氧化硅上的H 2 SO 4与N-碘代琥珀酰亚胺联用的硫糖苷活化来进行立体选择性，高产的糖基化策略。进行后期TEMPO介导的氧化，以形成所需的糖醛酸部分。还通过使用双糖基化方法制备了靶三糖的类似物。