p-methoxyphenyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside | 139526-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside
• 英文别名: p-methoxyphenyl 6-O-benzyl-2-deoxy-2-N-phthalimido-β-D-galactopyranoside；2-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-2-(4-methoxyphenoxy)-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 139526-00-4
• 化学式: C₂₈H₂₇NO₈
• 分子量: 505.524
• InChiKey: VNCVNJGDRVOTSC-ZJNQJMOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成 3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-D-galactopyranoside
  参考文献：
  名称：

  Studies Directed toward the Synthesis of Polysialogangliosides: The Regio- and Stereocontrolled Synthesis of Rationally Designed Fragments of the Tetrasialoganglioside GQ_1b⁺.

  摘要：

  The synthesis of suitably protected fragments of the tetrasialoganglioside GQ1b (I), i.e., 1 (alpha-NeuAc2 -->-8-alpha-NeuAc2 --> 3-beta-Gal1 --> 4Glc), 2 (alpha-NeuAc2 --> 8-alpha-NeuAc2 --> 3Gal), 3 (GalNAc), 4 (alpha-NeuAc2 --> 8NeuAc), 5 (beta-Gal1 -->- 3GalNAc), and 42 [beta-Gal1 --> 3-beta-GalNAc1 --> 4(alpha-NeuAc2 --> 3)beta-Gal --> 4Glc], is described. All are rationally designed so that the protecting groups can be regioselectively introduced and removed, as needed, before or after the stereoselective coupling of an appropriate pair of fragments. The syntheses of 1, 2, and 4 all feature stereoselective glycosylations by glycosyl donors that bear a C-3 thiophenoxy stereocontrolling auxiliary. Compound 3 was prepared from the D-glucosamine derivative 17 by way of a novel intramolecular nucleophilic displacement with inversion of configuration. Furthermore, model glycosylations of 4-hydroxygalactose derivatives, in which the thioglycoside 3 and the fluoride 40 served as glycosyl donors, were performed. The reaction of 3 with the glycosyl acceptor 30 gave the disaccharide 31 (GalNAc-beta-1 --> 4Gal), whereas that of 40 with 41 afforded the pentasaccharide 42.

  DOI：

  10.1021/jo00032a601
• 作为产物：
  描述：

  p-methoxyphenyl 6-O-benzyl-3,4-O-carbonyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以95%的产率得到p-methoxyphenyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside
  参考文献：
  名称：

  Studies Directed toward the Synthesis of Polysialogangliosides: The Regio- and Stereocontrolled Synthesis of Rationally Designed Fragments of the Tetrasialoganglioside GQ_1b⁺.

  摘要：

  The synthesis of suitably protected fragments of the tetrasialoganglioside GQ1b (I), i.e., 1 (alpha-NeuAc2 -->-8-alpha-NeuAc2 --> 3-beta-Gal1 --> 4Glc), 2 (alpha-NeuAc2 --> 8-alpha-NeuAc2 --> 3Gal), 3 (GalNAc), 4 (alpha-NeuAc2 --> 8NeuAc), 5 (beta-Gal1 -->- 3GalNAc), and 42 [beta-Gal1 --> 3-beta-GalNAc1 --> 4(alpha-NeuAc2 --> 3)beta-Gal --> 4Glc], is described. All are rationally designed so that the protecting groups can be regioselectively introduced and removed, as needed, before or after the stereoselective coupling of an appropriate pair of fragments. The syntheses of 1, 2, and 4 all feature stereoselective glycosylations by glycosyl donors that bear a C-3 thiophenoxy stereocontrolling auxiliary. Compound 3 was prepared from the D-glucosamine derivative 17 by way of a novel intramolecular nucleophilic displacement with inversion of configuration. Furthermore, model glycosylations of 4-hydroxygalactose derivatives, in which the thioglycoside 3 and the fluoride 40 served as glycosyl donors, were performed. The reaction of 3 with the glycosyl acceptor 30 gave the disaccharide 31 (GalNAc-beta-1 --> 4Gal), whereas that of 40 with 41 afforded the pentasaccharide 42.

  DOI：

  10.1021/jo00032a601

文献信息

• 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.