4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside | 918789-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside
• 英文别名: p-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-galactopyranoside；p-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside；4-methoxyphenyl 2-phthalimido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside；2-[(2S,4aR,6S,7R,8R,8aR)-8-hydroxy-6-(4-methoxyphenoxy)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]-2,3-dihydro-1H-isoindole-1,3-dione；2-[(2S,4aR,6S,7R,8R,8aR)-8-hydroxy-6-(4-methoxyphenoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione
• CAS: 918789-93-2
• 化学式: C₂₈H₂₅NO₈
• 分子量: 503.508
• InChiKey: SHSWKRFHEJOKLK-RLOIXHENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  103.76
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside 在 吡啶 、 sodium cyanoborohydride 、 nitrosonium tetrafluoroborate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 9.25h， 生成
  参考文献：
  名称：

  大肠杆菌O117：K98：H4 O抗原的五糖重复单元的合成。

  摘要：

  大肠杆菌O117：K98：H4菌株O抗原的五糖重复单元是使用顺序糖基化和[3 + 2]合成策略从适当保护的单糖中间体中合成的。硫代糖苷和糖基三氯乙酰亚氨酸酯衍生物已被用作糖基化中的糖基供体。

  DOI：

  10.3762/bjoc.10.287
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 在 碘 作用下， 以 乙腈 为溶剂， 反应 1.25h， 以85%的产率得到4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside
  参考文献：
  名称：

  Efficient Iodine‐Catalyzed Preparation of Benzylidene Acetals of Carbohydrate Derivatives

  摘要：

  An efficient preparation of benzylidene acetals of carbohydrate derivatives catalyzed by iodine has been developed. Yields were excellent in every case.

  DOI：

  10.1080/07328300802030837

文献信息

• Convergent synthesis of the hexasaccharide related to the repeating unit of the O-antigen from E. coli O120
  作者：Darshita Budhadev、Balaram Mukhopadhyay

  DOI：10.1039/c5ra20363e

  日期：——

  The hexasaccharide repeating unit of the O-antigen from E. coli O120 has been synthesized in the form of its 4-methoxyphenyl glycoside by a convergent [2 + 4] strategy.

  大肠杆菌O120的O-抗原的六糖重复单元已通过收敛[2 + 4]策略合成为其4-甲氧基苯基糖苷的形式。

• Stereoselective Glycosylations by Nitrosyl Tetrafluoroborate-Catalyzed Activation of Glycosyl Trichloroacetimidate Derivatives
  作者：Anup Misra、Abhijit Sau、Abhishek Santra

  DOI：10.1055/s-0032-1317135

  日期：——

  Efficient stereoselective glycosylation conditions have been developed by using nitrosyl tetrafluoroborate (NOBF4) promoted activation of glycosyl trichloroacetimidate derivatives. A series of mono- and disaccharide derivatives were synthesized in excellent yield, and high stereoselectivity at the glycosylation center was observed in every case.
• Concise synthesis of the pentasaccharide O-antigen corresponding to the Shiga toxin producing Escherichia coli O171
  作者：Pintu Kumar Mandal、Anup Kumar Misra

  DOI：10.1016/j.bioorg.2010.01.001

  日期：2010.4

  An expedient total synthesis of a pentasaccharide as its 4-methoxyphenyl glycoside corresponding to the Shiga toxin producing Escherichia coli O171 has been achieved for the first time in excellent yield. Most of the glycosylation steps are highly stereoselective. Stereoselective glycosylation of sialic acid derivative was obtained exploiting the nitrile effect of the solvent used. (C) 2010 Elsevier Inc. All rights reserved.
• Concise synthesis of a pentasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O102
  作者：Abhijit Sau、Debashis Dhara、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2013.06.005

  日期：2013.8

  An efficient synthetic strategy has been developed for the synthesis of a pentasaccharide repeating unit of the O-antigen of Escherichia coli O102 strain. The target pentasaccharide 1 has been synthesized using a [2+3] block glycosylation strategy. All glycosylation steps are highly stereoselective and high yielding. Concept of armed-disarmed and orthogonal glycosylation strategies has been applied during the synthesis. The target compound has been synthesized using the minimum number of steps. (C) 2013 Elsevier Ltd. All rights reserved.