Benzyl 3-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 151266-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl 3-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl] acetate
• CAS: 151266-85-2
• 化学式: C₂₃H₂₃NO₈
• 分子量: 441.438
• InChiKey: BCNQKZIKEGCKCO-MTSAVCEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Benzyl 3-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 、 dibenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl phosphite 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以49%的产率得到Benzyl 3-O-acetyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Towards the chemoenzymatic synthesis of lipid A

  摘要：

  New procedures have been developed for the synthesis of the two impotant components of lipid A; one is the lipase-catalyzed resolution of 3-hydrxytetradecanoic acid in tetrahydrofuran using vinyl acetate and the other is the synthesis of the disaccharide moiety using glycosylphosphite as the glycosylating reagent.

  DOI：

  10.1016/s0957-4166(00)80153-6
• 作为产物：
  描述：

  Benzyl 2-desoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 溶剂黄146 作用下， 反应 2.83h， 生成 Benzyl 3-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Towards the chemoenzymatic synthesis of lipid A

  摘要：

  New procedures have been developed for the synthesis of the two impotant components of lipid A; one is the lipase-catalyzed resolution of 3-hydrxytetradecanoic acid in tetrahydrofuran using vinyl acetate and the other is the synthesis of the disaccharide moiety using glycosylphosphite as the glycosylating reagent.

  DOI：

  10.1016/s0957-4166(00)80153-6

文献信息

• Synthesis of the Fungal Lipo-Chitooligosaccharide Myc-IV (C16:0, S), Symbiotic Signal of Arbuscular Mycorrhiza
  作者：Laura Gillard、Arnaud Stévenin、Isabelle Schmitz-Afonso、Boris Vauzeilles、François-Didier Boyer、Jean-Marie Beau

  DOI：10.1002/ejoc.201301015

  日期：2013.11

  A new synthesis of the fungal lipo-chitooligosaccharide Myc-IV (C16:0, S), which was recently reported to be a major symbiotic signalling molecule in arbuscular mycorrhiza, is described. Key steps include the oxidative cleavage of a 4,6-O-benzylidene acetal to prepare a disaccharidic glycosyl acceptor, and stereoselective glycosylations with 2-methyl-5-tert-butylphenyl thioglycosyl donors.

  描述了真菌脂壳寡糖 Myc-IV (C16:0, S) 的新合成方法，最近据报道它是丛枝菌根中的主要共生信号分子。关键步骤包括 4,6-O-亚苄基缩醛的氧化裂解以制备双糖基受体，以及与 2-甲基-5-叔丁基苯基硫代糖基供体的立体选择性糖基化。
• Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism
  作者：Hirosato Kondo、Shin Aoki、Yoshitaka Ichikawa、Randall L. Halcomb、Helena Ritzen、Chi-Huey Wong

  DOI：10.1021/jo00083a032

  日期：1994.2

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.