p-methoxyphenyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside | 943857-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside
• 英文别名: [(3S,4S,5R,6S)-4,5-diacetyloxy-6-(4-methoxyphenoxy)oxan-3-yl] acetate
• CAS: 943857-29-2
• 化学式: C₁₈H₂₂O₉
• 分子量: 382.367
• InChiKey: MKQVYQLMEWNXBF-FJIDUMEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside 在 五氟苯硼酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 p-methoxyphenyl 3-O-(2′,3′,4′-tri-O-acetyl-β-D-fucopyranosyl)-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
• 作为产物：
  描述：

  L-(+)-arabinose 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 p-methoxyphenyl 2,3,4-tri-O-acetyl-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

• 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。
• Lanthanum Trifluoromethane-sulfonate‐Catalyzed Facile Synthesis of Per‐<i>O</i>‐acetylated Sugars and Their One‐Pot Conversion to <i>S</i>‐Aryl and <i>O</i>‐Alkyl/Aryl Glycosides
  作者：Somnath Dasgupta‡、Vishal Kumar Rajput‡、Bimalendu Roy、Balaram Mukhopadhyay

  DOI：10.1080/07328300701298170

  日期：2007.4.30

  Lanthanum trifluoromethanesulfonate- catalyzed solvent-freeper-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.[GRAPHICS]